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| 2/2/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #1 410 Sprints - Winged, DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | - | - | - | - |
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| 2/3/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 4th | 2nd | - | 24th |
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| 2/5/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #4 (DIRTcar UMP Modifieds Gator Championship Night 1) 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 6th (DNF) | - | 2nd | 20th |
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| 2/7/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #6 (DIRTcar UMP Modifieds Gator Championship Night 3) 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 14th |
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| 3/5/2021 | Volusia Speedway Park - De Leon Springs, FL 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 20th |
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| 3/6/2021 | East Bay Raceway Park - Tampa, FL 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 1st | 5th | - | 21st (DNF) |
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| 3/12/2021 | Magnolia Motor Speedway - Columbus, MS 410 Sprints - Winged: World of Outlaws CRUSA Late Model Sportsman | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 13th |
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| 3/13/2021 | Revolution Park - Monroe, LA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 13th |
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| 3/19/2021 | Cotton Bowl Speedway - Paige, TX 410 Sprints - Winged: World of Outlaws Factory Stocks | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 14th |
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| 3/20/2021 | Cotton Bowl Speedway - Paige, TX 410 Sprints - Winged: World of Outlaws IMCA Southern SportMod | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 18th |
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| 3/27/2021 | Lake Ozark Speedway - Eldon, MO 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | 5th | 19th |
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| 4/2/2021 | Federated Auto Parts I-55 Raceway - Pevely, MO 410 Sprints - Winged: World of Outlaws B Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | 6th | 16th |
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| 4/3/2021 | Federated Auto Parts I-55 Raceway - Pevely, MO World of Outlaw Sprints & UMP Mods 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 6th | - | 10th |
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| 4/9/2021 | Kokomo Speedway - Kokomo, IN 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged | Results | | Jason Sides (410 Sprints - Winged) | 1st | 3rd | - | 14th |
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| 4/10/2021 | Tri-State Speedway - Haubstadt, IN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 17th |
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| 4/23/2021 | Bristol Motor Speedway - Bristol, TN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | 9th | - |
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| 4/23/2021 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 15th |
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| 4/25/2021 | Bristol Motor Speedway - Bristol, TN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 1st | 23rd (DNF) |
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| 4/30/2021 | I-70 Speedway - Odessa, MO 410 Sprints - Winged: World of Outlaws Non-Winged Sprints: POWRi WAR Sprints Midgets | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 18th |
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| 5/1/2021 | I-70 Speedway - Odessa, MO 410 Sprints - Winged: World of Outlaws Non-Winged Sprints: POWRi WAR Sprints Midgets | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 9th (DNF) | - |
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| 5/7/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC National Sprint Cars | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 6th | - |
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| 5/8/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws 410 Sprints - Non-Winged: USAC National Sprint Cars | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 7th | - |
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| 6/17/2021 | 34 Raceway - West Burlington, IA 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 17th |
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| 6/18/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA 410 Sprints - Winged: World of Outlaws A Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | - | 12th |
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| 6/19/2021 | Beaver Dam Raceway - Beaver Dam, WI 410 Sprints - Winged: World of Outlaws Lightning Sprints: IRA Lightning Sprints Semi-Pro Legends | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 2nd | 18th |
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| 6/21/2021 | Huset's Speedway - Brandon, SD The SHOWDOWN -HUSET'S 50 presented by BillionAuto.com 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 11th | - |
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| 6/22/2021 | Huset's Speedway - Brandon, SD THE SHOWDOWN - HUSET'S 50 - presented by BillionAuto.com 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | DNS | - | - | - |
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| 6/24/2021 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals - THE SHOWDOWN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 1st | - | - | 20th |
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| 6/25/2021 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals - THE SHOWDOWN 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 3rd | 4th | - | 7th |
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| 6/26/2021 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals - THE SHOWDOWN 410 Sprints - Winged: World of Outlaws | Postponed |
| 6/27/2021 | Jackson Motorplex - Jackson, MN 43rd Annual AGCO Jackson Nationals 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 13th |
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| 7/2/2021 | Cedar Lake Speedway - New Richmond, WI 410 Sprints - Winged: World of Outlaws 360 Sprints - Non-Winged: Traditional Sprint Car Series 305 Sprints - Non-Winged | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 5th |
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| 7/3/2021 | Cedar Lake Speedway - New Richmond, WI 410 Sprints - Winged: World of Outlaws Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 11th |
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| 7/10/2021 | Wilmot Raceway - Wilmot, WI 410 Sprints - Winged: World of Outlaws Lightning Sprints: IRA Lightning Sprints Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 6th | - | 10th |
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| 7/13/2021 | Attica Raceway Park - Attica, OH 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 5th | - |
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| 7/14/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | - | - | - | - |
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| 7/15/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 16th | - |
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| 7/17/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 13th |
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| 7/18/2021 | Eldora Speedway - Rossburg, OH The Knight Before 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 10th | - |
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| 7/20/2021 | Lernerville Speedway - Sarver, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 1st | 21st |
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| 7/23/2021 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 6th | - |
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| 7/24/2021 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 12th | - |
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| 7/30/2021 | Ransomville Speedway - Ransomville, NY 410 Sprints - Winged: World of Outlaws Sportsmans | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 13th |
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| 7/31/2021 | Weedsport Speedway - Weedsport, NY 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 4th | 20th |
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| 8/6/2021 | Federated Auto Parts I-55 Raceway - Pevely, MO 410 Sprints - Winged: World of Outlaws Midgets: POWRi National Midgets with POWRi West Midgets, POWRi | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 2nd | 16th |
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| 8/7/2021 | Federated Auto Parts I-55 Raceway - Pevely, MO 410 Sprints - Winged: World of Outlaws Midgets: POWRi National Midgets with POWRi West Midgets, POWRi | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 17th |
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| 8/11/2021 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged, Winged Sprints | Results | | Jason Sides (410 Sprints - Winged) | 2nd | - | - | 18th |
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| 8/13/2021 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged, Winged Sprints | Results | | Jason Sides (410 Sprints - Winged) | 11th | - | 19th | - |
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| 8/14/2021 | Knoxville Raceway - Knoxville, IA 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged, Winged Sprints | Results | | Jason Sides (410 Sprints - Winged) | - | - | - | - |
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| 8/21/2021 | Red River Valley Speedway - West Fargo, ND 410 Sprints - Winged: World of Outlaws B Modifieds, WISSOTA Late Model | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 2nd | 17th |
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| 8/22/2021 | Huset's Speedway - Brandon, SD World of Outlaws Sprint Car Series- Pioneer BIN BUSTER BASH 410 Sprints - Winged: World of Outlaws Street Stocks | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 6th | - |
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| 8/25/2021 | River Cities Speedway - Grand Forks, ND World of Outlaw Sprint Cars & NLRA Late Model Tour 410 Sprints - Winged: World of Outlaws B Modifieds, WISSOTA Late Model | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 15th |
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| 8/27/2021 | I-80 Speedway - Greenwood, NE 410 Sprints - Winged: World of Outlaws B Modifieds | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | - | 18th |
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| 8/29/2021 | Black Hills Speedway - Rapid City, SD 410 Sprints - Winged: World of Outlaws IMCA Hobby Stock, WISSOTA Street Stock | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 20th |
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| 9/3/2021 | Skagit Speedway - Burlington, WA SAGE FRUIT SKAGIT NATIONALS - WORLD OF OUTLAWS 410 Sprints - Winged: World of Outlaws Economy Midgets | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 19th |
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| 9/4/2021 | Skagit Speedway - Burlington, WA SAGE FRUIT SKAGIT NATIONALS - WORLD OF OUTLAWS 410 Sprints - Winged: World of Outlaws Economy Midgets | Results | | Jason Sides (410 Sprints - Winged) | 2nd | 5th | - | 17th |
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| 9/5/2021 | Skagit Speedway - Burlington, WA SAGE FRUIT SKAGIT NATIONALS - WORLD OF OUTLAWS 410 Sprints - Winged: World of Outlaws Economy Midgets | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 18th |
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| 9/6/2021 | Grays Harbor Raceway - Elma, WA WORLD OF OUTLAW call (844) 347-8849 for General Admission Tickets 410 Sprints - Winged: World of Outlaws 360 Sprints - Non-Winged: WSS - Wingless Sprint Series | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | - | 12th |
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| 9/10/2021 | Silver Dollar Speedway - Chico, CA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 19th |
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| 9/11/2021 | Silver Dollar Speedway - Chico, CA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 2nd | 19th |
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| 9/18/2021 | Kings Speedway - Hanford, CA Tom Tarlton Classic 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Jason Sides (410 Sprints - Winged) | 1st | 6th | - | 16th |
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| 9/24/2021 | Eldora Speedway - Rossburg, OH 410 Sprints - Winged: World of Outlaws Midgets: USAC National Midgets Silver Crown: USAC Silver Crown | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 22nd |
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| 9/25/2021 | Lernerville Speedway - Sarver, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 5th | - | - | 16th |
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| 10/1/2021 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | - | - | - | - |
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| 10/2/2021 | Williams Grove Speedway - Mechanicsburg, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 8th | - | 15th (DNF) | - |
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| 10/8/2021 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 7th | - | 14th | - |
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| 10/9/2021 | Port Royal Speedway - Port Royal, PA 410 Sprints - Winged: World of Outlaws | Results | | Jason Sides (410 Sprints - Winged) | 9th | - | 18th (DNF) | - |
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| 10/22/2021 | Lakeside Speedway - Kansas City, KS 410 Sprints - Winged: World of Outlaws Mod Lites | Results | | Jason Sides (410 Sprints - Winged) | 6th | - | 8th (DNF) | - |
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| 10/29/2021 | Lawton Speedway - Lawton, OK 410 Sprints - Winged: World of Outlaws USRA Limited Mods | Results | | Jason Sides (410 Sprints - Winged) | 3rd | - | - | 11th |
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| 10/30/2021 | Devil's Bowl Speedway - Mesquite, TX World of Outlaws Texas Nationals 410 Sprints - Winged: World of Outlaws USRA Limited Mods | Results | | Jason Sides (410 Sprints - Winged) | 4th | - | - | 13th |
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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 | | Jason Sides (410 Sprints - Winged) | 7th | - | 5th | - |
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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 | | Jason Sides (410 Sprints - Winged) | 7th | - | 10th | - |
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