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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 | | Ashton Winger (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 | | Ashton Winger (Dirt Super Late Models) | 8th | - | 11th | 11th |
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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 | | Ashton Winger (Dirt Super Late Models) | 9th (DNF) | - | 8th | 22nd (DNF) |
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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 | | Ashton Winger (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 | | Ashton Winger (Dirt Super Late Models) | 6th | - | 25th | - |
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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 | | Ashton Winger (Dirt Super Late Models) | 4th | - | 3rd | - |
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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 | | Ashton Winger (Dirt Super Late Models) | 5th | - | 11th | - |
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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 | | Ashton Winger (Dirt Super Late Models) | 4th | - | 1st | 10th |
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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 | | Ashton Winger (Dirt Super Late Models) | 11th | - | DNS | - |
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| 2/4/2021 | East Bay Raceway Park - Tampa, FL East Bay Winter Nationals CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series | Results | | Ashton Winger (CRUSA Dirt Late Models) | 1st | - | - | 4th |
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| 2/5/2021 | East Bay Raceway Park - Tampa, FL East Bay Winter Nationals CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series | Results | | Ashton Winger (CRUSA Dirt Late Models) | 3rd | - | 4th | - |
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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 | | Ashton Winger (DIRTcar Pro Late Models) | 5th | - | 4th | - |
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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 | | Ashton Winger (DIRTcar Pro Late Models) | 9th (DNF) | - | DNS | - |
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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 | | Ashton Winger (Dirt Super Late Models) | 6th | - | DNS | 27th |
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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 | | Ashton Winger (Dirt Super Late Models) | DNS | - | DNS | - |
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| 3/12/2021 | Boothill Speedway - Greenwood, LA Rescheduled 2nd Annual Ronny Adams Memorial - Night #1 Factory Stocks, Dirt Late Models, Limited Modified | Results | | Ashton Winger (Dirt Late Models) | 3rd | - | - | 7th |
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| 3/13/2021 | Boothill Speedway - Greenwood, LA Rescheduled 2nd Annual Ronny Adams Memorial - Night #2 Factory Stocks, Dirt Late Models, CRUSA Dirt Late Models | Results | | Ashton Winger (Dirt Late Models) | 2nd | - | - | 2nd |
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| 3/19/2021 | Old No 1 Speedway - Harrisburg, AR COMP CAM LATE MODELS Hobby Stocks, Stock Cars, A Modifieds, Street Stocks, Dirt Late Models, Hornets | Results | | Ashton Winger (Dirt Late Models) | 3rd | - | - | 6th |
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| 3/20/2021 | I-30 Speedway - Little Rock, AR Winged Outlaw, Dirt Late Models | Results | | Ashton Winger (Dirt Late Models) | 2nd | - | - | 2nd |
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| 4/2/2021 | Poplar Bluff Motorsports Park - Poplar Bluff, MO COMP Cams Super Dirt Series Dirt Late Models | Results | | Ashton Winger (Dirt Late Models) | 6th | - | 4th | 5th |
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| 4/3/2021 | Legit Speedway Park - West Plains, MO COMP Cams Super Dirt Series Hobby Stocks, A Modifieds, Dirt Late Models, Economy Late Models, Limited Sport Mod, Super Stocks | Results | | Ashton Winger (Dirt Late Models) | 2nd | - | - | 6th |
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| 4/8/2021 | Lucas Oil Speedway - Wheatland, MO 8th Annual Spring Nationals Dirt Super Late Models: Lucas Oil MLRA USRA Modifieds, USRA Stock Cars | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | - |
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| 4/9/2021 | Lincoln Speedway - Lincoln, IL Fall Nationals 2020 Makeup Dirt Super Late Models, DIRTcar UMP Modifieds, B Modifieds, Hornets | Results | | Ashton Winger (Dirt Super Late Models) | 6th (DNF) | - | - | 14th (DNF) |
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| 4/13/2021 | I-80 Speedway - Greenwood, NE Tuesday Tickler with Lucas Oil MLRA Dirt Super Late Models: Lucas Oil MLRA A Modifieds, Dirt Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | - | - | 3rd |
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| 4/14/2021 | Stuart Speedway - Stuart, IA Lucas Oil MLRA Late Models Dirt Super Late Models: Lucas Oil MLRA IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Ashton Winger (Dirt Super Late Models) | 4th | - | - | 7th |
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| 4/15/2021 | Davenport Speedway - Davenport, IA Annual Event Dirt Super Late Models: Lucas Oil MLRA | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | - | - | 4th |
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| 4/16/2021 | 34 Raceway - West Burlington, IA Prelude to the Slocum Dirt Super Late Models: Lucas Oil MLRA 305 Sprints - Winged, Stock Cars, 2WD Trucks | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | - | - | 7th |
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| 4/17/2021 | 34 Raceway - West Burlington, IA Slocum 50 presented by The Outpost Bar & Grill Dirt Super Late Models: Lucas Oil MLRA 305 Sprints - Winged, Stock Cars | Results | | Ashton Winger (Dirt Super Late Models) | 7th | - | 5th | 18th |
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| 5/1/2021 | Clayhill Motorsports Park - Atwood, TN | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 3rd |
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| 5/7/2021 | Batesville Motor Speedway - Locust Grove, AR Joe Garrison Memorial Dirt Late Models, IMCA Modified | Results | | Ashton Winger (Dirt Late Models) | 1st | - | - | 17th |
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| 5/8/2021 | Batesville Motor Speedway - Locust Grove, AR Bad Boy 98 Dirt Late Models | Results | | Ashton Winger (Dirt Late Models) | 3rd | - | - | 19th (DNF) |
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| 5/22/2021 | Senoia Raceway - Senoia, GA Roscoe Smith Classic Dirt Super Late Models: Southern All Stars Hobby Stocks, Sportsmans, Street Stocks, Dirt Late Models, Pony Stock, Dirt Crate Late Models, Asphalt Bombers | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 1st |
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| 5/29/2021 | Thunderhill Raceway - Summertown, TN Whoopin' the Wuhan Flu 50 (Southern All Stars) Dirt Super Late Models: Southern All Stars Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, Outlaw Hobby Stocks, CRUSA Modified Sportsman, Speedstr | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 5th |
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| 5/31/2021 | 411 Motor Speedway - Seymour, TN Scott Sexton Memorial Valvoline Iron Man Series Dirt Super Late Models: Iron-Man Late Model Series Sportsmans, A Modifieds, Street Stocks, Vintage Modifieds, Dirt Crate Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 3rd |
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| 6/15/2021 | Brownstown Speedway - Brownstown, IN DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Ashton Winger (DIRTcar Late Models) | 4th | - | - | 8th |
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| 6/16/2021 | Peoria Speedway - Peoria, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Ashton Winger (DIRTcar Late Models) | 5th | - | 1st | 7th |
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| 6/17/2021 | Kankakee County Speedway - Kankakee, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Ashton Winger (DIRTcar Late Models) | 3rd | - | - | 9th |
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| 6/18/2021 | Tri City Speedway - Granite City, IL UMP Summer Nationals UMP LM $10,000 with Summit Mods $1,500 & BMods $1,000 DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals B Modifieds | Results | | Ashton Winger (DIRTcar Late Models) | DNS | - | 1st | 16th |
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| 6/19/2021 | Fairbury Speedway - Fairbury, IL DIRTcar Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals DIRTcar Sportsmans | Results | | Ashton Winger (DIRTcar Late Models) | 2nd | - | - | 10th |
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| 6/23/2021 | LaSalle Speedway - Lasalle, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Ashton Winger (DIRTcar Late Models) | 3rd | - | - | 8th |
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| 6/25/2021 | Sycamore Speedway - Sycamore, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Ashton Winger (DIRTcar Late Models) | 1st | - | - | 3rd |
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| 6/30/2021 | Beaver Dam Raceway - Beaver Dam, WI DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals | Results | | Ashton Winger (DIRTcar Late Models) | 3rd | - | - | 3rd |
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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 | | Ashton Winger (DIRTcar Late Models) | 2nd | - | - | 10th |
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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 | | Ashton Winger (DIRTcar Late Models) | 3rd | - | - | 4th |
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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 | | Ashton Winger (DIRTcar Late Models) | 1st | - | - | 7th |
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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 | | Ashton Winger (DIRTcar Late Models) | 2nd | - | - | 6th |
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| 7/6/2021 | Knox County Fairgrounds - Knoxville, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Ashton Winger (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 | | Ashton Winger (DIRTcar Late Models) | 5th | - | 2nd | 10th |
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| 7/8/2021 | Macon Speedway - Macon, IL Herald & Review 100 Featuring the Summer Nationals Hell Tour DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals B Modifieds | Results | | Ashton Winger (DIRTcar Late Models) | 8th | - | - | 10th |
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| 7/9/2021 | Farmer City Raceway - Farmer City, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Street Stocks, Pro Late Model | Results | | Ashton Winger (DIRTcar Late Models) | 10th | - | - | 12th |
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| 7/14/2021 | Circle City Raceway - Indianapolis, IN DIRTCar Summer Nationals - Super Late Models, UMP Modifieds DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Ashton Winger (DIRTcar Late Models) | 3rd | - | - | 6th |
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| 7/15/2021 | Thunderbird Raceway - Muskegon, MI DIRTcar Summer National Hell Tour Returns along with Summit Modified Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Sport Compact | Results | | Ashton Winger (DIRTcar Late Models) | 1st | - | - | 1st |
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| 7/17/2021 | Oakshade Raceway - Wauseon, OH Birthday Race DIRTcar Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Factory Stocks | Results | | Ashton Winger (DIRTcar Late Models) | 1st | - | - | 1st |
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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 | | Ashton Winger (Dirt Super Late Models) | - | - | - | 16th |
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| 7/22/2021 | Springfield Raceway - Springfield, MO GREENLAWN FUNERAL HOMES PRESENTS DIRTcar SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals Midwest Modifieds, Dirt Late Models, Limited Sport Mod, USRA B-Mods | Results | | Ashton Winger (DIRTcar Late Models) | 2nd | - | - | 2nd |
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| 7/23/2021 | Tri City Speedway - Granite City, IL "Russ Wallace Memorial" Summer Nationals Race #2 UMP LM $10,000,UMP Mod $1,500 & BMods $1,000 DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals B Modifieds | Results | | Ashton Winger (DIRTcar Late Models) | 2nd | - | - | 3rd |
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| 7/24/2021 | Clarksville Speedway - Clarksville, TN DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Ashton Winger (DIRTcar Late Models) | 1st | - | - | 1st |
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| 7/25/2021 | Richmond Raceway (KY) - Richmond, KY DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Ashton Winger (DIRTcar Late Models) | 2nd | - | - | 2nd |
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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 | | Ashton Winger (Dirt Super Late Models) | - | - | - | 18th |
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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 | | Ashton Winger (Dirt Super Late Models) | - | - | - | 12th |
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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 | | Ashton Winger (Dirt Super Late Models) | - | - | - | 1st |
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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 | | Ashton Winger (Dirt Super Late Models) | 1st | 2nd | - | - |
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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 | | Ashton Winger (Dirt Super Late Models) | - | - | - | 3rd |
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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 | | Ashton Winger (DIRTcar Late Models) | 5th | - | - | 5th |
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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 | | Ashton Winger (DIRTcar Late Models) | 2nd | - | - | 3rd |
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| 8/18/2021 | Butler Speedway - Quincy, MI DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Ashton Winger (DIRTcar Late Models) | 1st | - | - | 2nd |
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| 8/19/2021 | I-96 Speedway - Lake Odessa, MI Summer Nationals Hell Tour | Cyber Stocks $500 To Win - $100 To Start DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Sport Compact | Results | | Ashton Winger (DIRTcar Late Models) | 3rd | - | - | 3rd |
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| 8/20/2021 | Tri-City Motor Speedway - Auburn, MI DIRTcar Summer Nationals HELL TOUR & PRO STOCK NIGHT $3000 TO WIN DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Factory Stocks, Hobby Stocks, Sportsmans, Mini Wedge, Mini Outlaws | Results | | Ashton Winger (DIRTcar Late Models) | 1st | - | - | 1st |
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| 8/21/2021 | Merritt Speedway - Merritt, MI DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Lightning Sprints: Great Lakes Lightning Sprints Factory Stocks, Hobby Stocks, Sportsmans, Mini Wedge, Mini Outlaws | Results | | Ashton Winger (DIRTcar Late Models) | 1st | - | - | 1st |
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| 8/28/2021 | Senoia Raceway - Senoia, GA SAS Head Family Memorial and NRVA Vintage Thunder Dirt Super Late Models: Southern All Stars Hobby Stocks, Sportsmans, Street Stocks, Dirt Late Models, Vintage Full Body Stock Cars, Vintage Modifieds, Pony Stock, Dirt Crate Late Models, Asphalt Bombers | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 1st |
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| 9/5/2021 | Eldora Speedway - Rossburg, OH | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 6th |
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| 9/8/2021 | Eldora Speedway - Rossburg, OH | Results | | Ashton Winger (DIRTcar Late Models) | - | - | - | 16th |
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| 9/9/2021 | Eldora Speedway - Rossburg, OH | Results | | Ashton Winger (DIRTcar Late Models) | - | - | - | 16th |
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| 9/10/2021 | Eldora Speedway - Rossburg, OH | Results | | Ashton Winger (DIRTcar Late Models) | - | - | - | 9th |
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| 9/11/2021 | Eldora Speedway - Rossburg, OH | Results | | Ashton Winger (DIRTcar Late Models) | - | - | - | 27th |
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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 | | Ashton Winger (Dirt Super Late Models) | - | - | 6th | - |
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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 | | Ashton Winger (Dirt Super Late Models) | 4th | - | - | 16th |
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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 | | Ashton Winger (Dirt Super Late Models) | - | - | - | 1st |
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| 10/9/2021 | West Virginia Motor Speedway - Mineral Wells, WV RWT RaceFest (Feature) Dirt Super Late Models: Iron-Man Late Model Series B Modifieds: The Road Warrior Sport Mod Tour | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 18th |
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| 10/10/2021 | West Virginia Motor Speedway - Mineral Wells, WV Racefest World Championship Dirt Super Late Models: Iron-Man Late Model Series | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 22nd |
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| 10/16/2021 | Ultimate Motorsports & RV Park - Elkin, NC | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 2nd |
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| 10/21/2021 | Senoia Raceway - Senoia, GA Hence & Reba Pollard Memorial Night 1 Stock Cars | Results | | Ashton Winger (Stock Cars) | - | - | - | - |
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| 10/22/2021 | Senoia Raceway - Senoia, GA SAS Billy Clanton Classic Dirt Super Late Models, Hobby Stocks, Sportsmans, Street Stocks, Dirt Late Models, Pony Stock, Dirt Crate Late Models, Dirt Limited Late Models, Asphalt Bombers | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 1st |
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| 10/23/2021 | Senoia Raceway - Senoia, GA Hence & Reba Pollard Memorial Night 3 Dirt Super Late Models: Southern All Stars Hobby Stocks, Sportsmans, Street Stocks, Dirt Late Models, Pony Stock, Dirt Crate Late Models, Asphalt Bombers | Results | | Ashton Winger (Dirt Super Late Models) | 1st | - | - | 1st |
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| 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 | | Ashton Winger (Dirt Super Late Models) | 7th | - | 15th | - |
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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 | | Ashton Winger (Dirt Super Late Models) | 5th | - | 3rd | 15th |
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| 11/11/2021 | Senoia Raceway - Senoia, GA Peach State Classic Dirt Super Late Models, Hobby Stocks, Sportsmans, Street Stocks, Pony Stock, Dirt Crate Late Models, Asphalt Bombers | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | - |
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| 11/12/2021 | Senoia Raceway - Senoia, GA Peach State Classic Dirt Super Late Models, Hobby Stocks, Sportsmans | Results | | Ashton Winger (Dirt Super Late Models) | 2nd | - | - | 5th |
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| 11/13/2021 | Senoia Raceway - Senoia, GA Peach State Classic Dirt Super Late Models, Dirt Crate Late Models, Asphalt Bombers | Results | | Ashton Winger (Dirt Super Late Models) | 1st | - | - | 3rd |
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| 11/19/2021 | Southern Raceway - Milton, FL King of the Sandbox Friday Night Dirt Super Late Models, Stock Cars, Vintage Full Body Stock Cars, Hornets | Results | | Ashton Winger (Dirt Super Late Models) | 1st | - | - | 1st |
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| 11/20/2021 | Southern Raceway - Milton, FL King of the Sandbox Saturday Night Dirt Super Late Models, Sportsmans, CRUSA Street Stocks, Pure Stock | Results | | Ashton Winger (Dirt Super Late Models) | 1st | - | - | 14th |
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