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| 1/13/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Practice Night Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 1/14/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Night #1 Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 4th | - | - | 9th |
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| 1/15/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Night #2 Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Rain Out |
| 1/16/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Night #3 Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 7th |
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| 1/21/2021 | All-Tech Raceway - Lake City, FL Winter Nationals Practice Night Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 1/22/2021 | All-Tech Raceway - Lake City, FL Winter Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Rain Out |
| 1/23/2021 | All-Tech Raceway - Lake City, FL Winter Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 5th |
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| 1/24/2021 | East Bay Raceway Park - Tampa, FL 45th Annual Wrisco Industries Winternationals presented by Lucas Oil Practice Night Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 1/25/2021 | East Bay Raceway Park - Tampa, FL 45th Annual Wrisco Industries Winternationals presented by Lucas Oil Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 1/26/2021 | East Bay Raceway Park - Tampa, FL 45th Annual Wrisco Industries Winternationals presented by Lucas Oil Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 18th |
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| 1/27/2021 | East Bay Raceway Park - Tampa, FL 45th Annual Wrisco Industries Winternationals presented by Lucas Oil Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 9th |
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| 1/28/2021 | East Bay Raceway Park - Tampa, FL 45th Annual Wrisco Industries Winternationals presented by Lucas Oil Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 12th |
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| 1/29/2021 | East Bay Raceway Park - Tampa, FL 45th Annual Wrisco Industries Winternationals presented by Lucas Oil Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 4th | - | 2nd | 15th |
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| 1/30/2021 | East Bay Raceway Park - Tampa, FL 45th Annual Wrisco Industries Winternationals presented by Lucas Oil Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 2/1/2021 | Ocala Speedway - Ocala, FL Winter Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 14th |
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| 2/2/2021 | Ocala Speedway - Ocala, FL Winter Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 4th | - | - | 9th |
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| 2/8/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #7 (DIRTcar UMP Modifieds Gator Championship Night 4) DIRTcar UMP Modifieds, DIRTcar Pro Late Models | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 6th | | Brandon Sheppard (DIRTcar Pro Late Models) | 2nd | - | - | 6th |
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| 2/9/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #8 DIRTcar Big Block Modifieds: Super DIRTCar Series DIRTcar Pro Late Models | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 4th | | Brandon Sheppard (DIRTcar Pro Late Models) | 1st | - | - | 4th |
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| 2/10/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #9 Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 20th |
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| 2/11/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #10 Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 4th | - | 2nd | 6th |
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| 2/12/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #11 Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 4th | - | - | 11th |
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| 3/6/2021 | Smoky Mountain Speedway - Maryville, TN 8th Annual Tennessee Tipoff Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models, Hornets | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 8th |
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| 3/20/2021 | Brownstown Speedway - Brownstown, IN Indiana Icebreaker (Finished on 9/23/21) Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | - |
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| 3/21/2021 | Atomic Speedway - Chillicothe, OH Buckeye Spring 50 Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 12th |
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| 3/26/2021 | Cherokee Speedway - Gaffney, SC ROCK GAULT MEMORIAL Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 4/2/2021 | Farmer City Raceway - Farmer City, IL Triple Qualifying Features $600 to win $100 to start Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: Summit American Modified Series Street Stocks, Dirt Late Models, Pro Late Model | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 5th |
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| 4/3/2021 | Farmer City Raceway - Farmer City, IL $2500 to win $150 to start Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: Summit American Modified Series Dirt Late Models, Pro Late Model | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 3rd |
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| 4/9/2021 | Bristol Motor Speedway - Bristol, TN WORLD OF OUTLAWS BRISTOL BASH Dirt Super Late Models: World of Outlaws - Late Models A Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 3rd |
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| 4/11/2021 | Bristol Motor Speedway - Bristol, TN WORLD OF OUTLAWS BRISTOL BASH Dirt Super Late Models: World of Outlaws - Late Models A Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 13th |
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| 4/17/2021 | Hagerstown Speedway - Hagerstown, MD Nininger Tribute Dirt Super Late Models: Lucas Oil Late Model Dirt Series Pure Stock | Results | | Brandon Sheppard (Dirt Super Late Models) | 7th | - | 6th | 11th |
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| 4/18/2021 | Port Royal Speedway - Port Royal, PA Port Royal Speedway Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 4/23/2021 | Richmond Raceway (KY) - Richmond, KY World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 9th |
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| 4/30/2021 | Boone Speedway - Boone, IA Hawkeye 100 World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 2nd |
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| 5/1/2021 | Boone Speedway - Boone, IA Hawkeye 100 World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 3rd |
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| 5/7/2021 | Mississippi Thunder Speedway - Fountain City, WI Dairyland Showdown with World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 1st |
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| 5/8/2021 | Mississippi Thunder Speedway - Fountain City, WI Dairyland Showdown with World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 3rd |
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| 5/12/2021 | Brownstown Speedway - Brownstown, IN Dirt Super Late Models: Castrol FloRacing Night in America DIRTcar UMP Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 4th | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 4th |
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| 5/14/2021 | Farmer City Raceway - Farmer City, IL Farmer City 74 DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Brandon Sheppard (Dirt Late Models) | 1st | - | - | 1st |
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| 5/15/2021 | Fairbury Speedway - Fairbury, IL Spring Showcase DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 4th |
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| 5/21/2021 | Port Royal Speedway - Port Royal, PA HUEY WILCOXON MEMORIAL Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 3rd |
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| 5/22/2021 | Port Royal Speedway - Port Royal, PA Dirt Super Late Models: World of Outlaws - Late Models 410 Sprints - Winged, Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 15th |
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| 5/25/2021 | Tri City Speedway - Granite City, IL Castrol FloRacing Late Model Night in America $10,000 with UMP Mods $1,500 Dirt Super Late Models: Castrol FloRacing Night in America DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 5th | - | - | 10th | | Brandon Sheppard (DIRTcar Late Models) | 5th | - | - | 10th |
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| 5/27/2021 | Lucas Oil Speedway - Wheatland, MO 8th Annual Cowboy Classic Dirt Super Late Models: Lucas Oil MLRA with Lucas Oil Late Model Dirt Series USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 4th |
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| 5/28/2021 | Lucas Oil Speedway - Wheatland, MO The Tribute to Don and Billie Gibson Dirt Super Late Models: Lucas Oil MLRA with Lucas Oil Late Model Dirt Series USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 4th |
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| 5/29/2021 | Lucas Oil Speedway - Wheatland, MO 29th Annual Lucas Oil Show-Me 100 Dirt Super Late Models: Lucas Oil MLRA with Lucas Oil Late Model Dirt Series USRA Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 2nd |
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| 5/30/2021 | Spoon River Speedway - Canton, IL DIRTcar Late Models: MARS - Midwest Auto Racing Series Dirt Super Late Models | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 1st |
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| 6/4/2021 | Circle City Raceway - Indianapolis, IN World of Outlaws Morton Buildings Late Models, Legends, United CC ModLites Dirt Super Late Models: World of Outlaws - Late Models Mod Lites: United CC Modified Series Pro Legends | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 6/5/2021 | Plymouth Speedway - Plymouth, IN World of Outlaw Late Models ~ Mods & 4 Cyl Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds, Asphalt Mini Stocks | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 4th |
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| 6/9/2021 | Eldora Speedway - Rossburg, OH | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 12th |
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| 6/10/2021 | Eldora Speedway - Rossburg, OH | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 5th |
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| 6/11/2021 | Eldora Speedway - Rossburg, OH | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 8th |
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| 6/12/2021 | Eldora Speedway - Rossburg, OH | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 22nd (DNF) |
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| 6/17/2021 | Stateline Speedway - Busti, NY World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 6/18/2021 | Thunder Mountain Speedway - Brookville, PA CONNOR BOBIK MEMORIAL Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 6/19/2021 | Selinsgrove Raceway Park - Sellinsgrove, PA Late Model National Open Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 6/24/2021 | Lernerville Speedway - Sarver, PA "Bill Emig Memorial" - Night 1 Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 1st |
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| 6/25/2021 | Lernerville Speedway - Sarver, PA "Bill Emig Memorial" - Night 2 Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 5th |
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| 6/26/2021 | Lernerville Speedway - Sarver, PA "Bill Emig Memorial" - Night 3 Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 5th |
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| 6/30/2021 | Beaver Dam Raceway - Beaver Dam, WI DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals | Results | | Brandon Sheppard (DIRTcar Late Models) | 2nd | - | - | 2nd |
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| 7/1/2021 | Davenport Speedway - Davenport, IA DIRTcar Summer Nationals Hell Tour DIRTcar Late Models: DIRTcar Summer Nationals A Modifieds, Street Stocks, Dirt Late Models | Results | | Brandon Sheppard (DIRTcar Late Models) | 4th | - | - | 3rd |
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| 7/2/2021 | Dirt Oval at Route 66 - Joliet, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Brandon Sheppard (DIRTcar Late Models) | 2nd | - | - | 6th |
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| 7/3/2021 | Brownstown Bullring - Brownstown, IL $3000 to win $200 to start DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals with Summit American Modified Series | Results | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 1st |
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| 7/4/2021 | Lincoln Speedway - Lincoln, IL DIRTcar Summer Nationals Hell Tour "Graue Chevrolet Showdown" with FIREWORKS!!! DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals 305 Sprints - Winged, Dirt Super Late Models | Results | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 1st |
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| 7/7/2021 | Spoon River Speedway - Canton, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Brandon Sheppard (DIRTcar Late Models) | 2nd | - | - | 3rd |
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| 7/9/2021 | Jackson Motorplex - Jackson, MN World of Outlaws Morton Buildings Late Model Series Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models: Tri-State Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 7/10/2021 | Jackson Motorplex - Jackson, MN World of Outlaws Morton Buildings Late Model Series Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models: Tri-State Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 7/13/2021 | Gondik Law Speedway - Superior, WI World of Outlaws Late Model Special Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Modifieds, WISSOTA Hornet | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 7/16/2021 | River Cities Speedway - Grand Forks, ND World of Outlaw Late Models & NOSA Sprint Cars 410 Sprints - Winged: Northern Outlaw Sprint Association Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Street Stock | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 5th |
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| 7/17/2021 | I-94 Speedway - Fergus Falls, MN World of Outlaw Late Models and Steffes Street Stock Special Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 7/18/2021 | Red Cedar Speedway - Menomonie, WI World of Outlaws Late Models & $1,000 to Win Open Modifieds w/ Limited Late Models Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, Dirt Limited Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 7/20/2021 | I-80 Speedway - Greenwood, NE I-80 Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | 2nd | 22nd |
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| 7/21/2021 | I-80 Speedway - Greenwood, NE I-80 Speedway Silver Dollar Nationals - EAST/WEST Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 13th |
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| 7/22/2021 | I-80 Speedway - Greenwood, NE Al Belt Custom Homes I-80 Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series Stock Cars | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 13th |
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| 7/23/2021 | I-80 Speedway - Greenwood, NE Imperial Tile Silver Dollar Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds, IMCA Modified | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | - |
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| 7/24/2021 | I-80 Speedway - Greenwood, NE Imperial Tile Silver Dollar Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds, IMCA Modified | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 6th |
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| 7/30/2021 | Fairbury Speedway - Fairbury, IL PRAIRIE DIRT CLASSIC Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 7/31/2021 | Fairbury Speedway - Fairbury, IL PRAIRIE DIRT CLASSIC Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: DIRTcar Modified Nationals DIRTcar Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 5th |
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| 8/3/2021 | Outagamie Speedway - Seymour, WI FVP Platinum Batteries Showdown featuring the Morton Buildings World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models IMCA Modified, IMCA Stock Car | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 2nd |
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| 8/5/2021 | Cedar Lake Speedway - New Richmond, WI 34th Annual USA Nationals Night 1 Dirt Super Late Models: World of Outlaws - Late Models USRA Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 3rd |
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| 8/6/2021 | Cedar Lake Speedway - New Richmond, WI 34th Annual USA Nationals Night 2 Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | 5th | - | - |
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| 8/7/2021 | Cedar Lake Speedway - New Richmond, WI 34th Annual USA Nationals Night 3 Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 5th |
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| 8/13/2021 | Highland Speedway - Highland, IL Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals B Modifieds, Street Stocks | Results | | Brandon Sheppard (DIRTcar Late Models) | 2nd | - | - | 1st |
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| 8/14/2021 | Federated Auto Parts I-55 Raceway - Pevely, MO DIRTcar Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals B Modifieds | Results | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 2nd |
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| 8/19/2021 | Orange County Fair Speedway - Middletown, NY World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st |
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| 8/20/2021 | Williams Grove Speedway - Mechanicsburg, PA Dirt Super Late Models: World of Outlaws - Late Models 410 Sprints - Winged | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 6th |
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| 8/21/2021 | Sharon Speedway - Hartford, OH BATTLE AT THE BORDER Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 8/22/2021 | Eriez Speedway - Erie, PA World of Outlaw Super Late Models, E-Mod Special, Challenger Challenge Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds, Sport Compact | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 8/26/2021 | Davenport Speedway - Davenport, IA Quad Cities 150 presented by Hoker Trucking Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, B Modifieds, IMCA Modified | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 7th |
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| 8/27/2021 | Davenport Speedway - Davenport, IA Quad Cities 150 presented by Hoker Trucking Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, B Modifieds, IMCA Modified | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 1st |
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| 8/28/2021 | Davenport Speedway - Davenport, IA Quad Cities 150 presented by Hoker Trucking Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, B Modifieds, IMCA Modified | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 4th |
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| 9/2/2021 | Cherokee Speedway - Gaffney, SC ROCK GAULT MEMORIAL Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 10th |
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| 9/3/2021 | Lavonia Speedway - Lavonia, GA World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 3rd |
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| 9/4/2021 | Volunteer Speedway - Bulls Gap, TN World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 9/8/2021 | Eldora Speedway - Rossburg, OH | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 3rd |
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| 9/9/2021 | Eldora Speedway - Rossburg, OH | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 18th |
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| 9/10/2021 | Eldora Speedway - Rossburg, OH | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 3rd |
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| 9/11/2021 | Eldora Speedway - Rossburg, OH | Results | | Brandon Sheppard (DIRTcar Late Models) | - | - | - | 6th |
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| 9/13/2021 | Fairbury Speedway - Fairbury, IL FALS One for the Road Castrol Flo Racing Night in America Dirt Super Late Models: Castrol FloRacing Night in America DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 1st | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 1st |
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| 9/16/2021 | Knoxville Raceway - Knoxville, IA 17th Lucas Oil Late Model Knoxville Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 3rd | - | - | 10th |
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| 9/17/2021 | Knoxville Raceway - Knoxville, IA 17th Lucas Oil Late Model Knoxville Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 9/18/2021 | Knoxville Raceway - Knoxville, IA 17th Lucas Oil Late Model Knoxville Nationals Dirt Super Late Models: SLMR Late Model Series with Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 5th |
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| 9/23/2021 | Brownstown Speedway - Brownstown, IN Indiana Icebreaker (Continued from 3/20/21) Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 1st |
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| 9/24/2021 | Brownstown Speedway - Brownstown, IN Night Before the Jackson Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 2nd | - | - | 3rd |
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| 9/25/2021 | Brownstown Speedway - Brownstown, IN 42nd Annual Jackson 100 Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 4th | - | - | 13th |
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| 10/1/2021 | Cherokee Speedway - Gaffney, SC MIKE DUVALL MEMORIAL Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | 2nd |
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| 10/2/2021 | Senoia Raceway - Senoia, GA Regular Show Dirt Super Late Models: World of Outlaws - Late Models Sportsmans, Street Stocks | Results | | Brandon Sheppard (Dirt Super Late Models) | 4th | - | - | 6th |
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| 10/9/2021 | Fairbury Speedway - Fairbury, IL FALS Frenzy DIRTcar Late Models, DIRTcar UMP Modifieds, Pro Late Model | Results | | Brandon Sheppard (DIRTcar Late Models) | 1st | - | - | 2nd |
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| 10/15/2021 | Portsmouth Raceway Park - Portsmouth, OH 41st Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Pro Legends, Economy Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | - | - |
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| 10/16/2021 | Portsmouth Raceway Park - Portsmouth, OH 41st Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Pro Legends, Economy Late Models | Results | | Brandon Sheppard (Dirt Super Late Models) | 10th | - | - | - |
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| 10/30/2021 | 81 Speedway - Park City, KS 2nd Annual USMTS Modified Spooktacular A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, USRA Modifieds | Results | | Brandon Sheppard (A Modifieds) | 1st | - | - | 5th | | Brandon Sheppard (USRA Modifieds) | - | - | - | 5th |
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| 11/4/2021 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Postponed |
| 11/5/2021 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 2nd |
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| 11/6/2021 | The Dirt Track at Charlotte - Concord, NC 410 Sprints - Winged: World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 12/2/2021 | The Dome at America's Center - St. Louis, MO Castrol Gateway Dirt Nationals Midgets, Dirt Super Late Models, A Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | 1st | - | - | 16th |
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| 12/4/2021 | The Dome at America's Center - St. Louis, MO Midgets, Dirt Super Late Models, A Modifieds | Results | | Brandon Sheppard (Dirt Super Late Models) | - | - | 1st | 4th |
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