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| 1/3/2020 | Vado Speedway Park - Vado, NM Battle at the Border Dirt Super Late Models: World of Outlaws - Late Models USRA B-Mods, USRA Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | 2nd | - | - | 9th |
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| 1/4/2020 | Vado Speedway Park - Vado, NM Battle at the Border Dirt Super Late Models: World of Outlaws - Late Models USRA B-Mods, USRA Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | 4th | - | - | 14th |
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| 1/5/2020 | Vado Speedway Park - Vado, NM Battle at the Border Dirt Super Late Models: World of Outlaws - Late Models USRA B-Mods, USRA Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | 2nd | - | - | 18th |
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| 2/10/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Ashton Winger (DIRTcar Late Models) | 3rd | - | - | 13th |
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| 2/11/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar Late Models, Dirt Big Block Modifieds | Results | | Ashton Winger (DIRTcar Late Models) | 6th | - | 4th | - |
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| 2/12/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | - | - | 14th |
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| 2/13/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | 4th | - | DNS | 18th |
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| 2/14/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | 2nd | - | - | 17th |
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| 2/15/2020 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Big Block Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | 7th | - | 4th | 19th |
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| 3/1/2020 | Cherokee Speedway - Gaffney, SC March Madness Day 2 Dirt Super Late Models, CRUSA Dirt Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | - | - | 10th |
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| 3/6/2020 | Duck River Raceway Park - Shelbyville, TN World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models Hobby Stocks, Street Stocks, Dirt Late Models, Pro Late Model, Pony Stock, Dirt Crate Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 5th | - | 1st | 22nd (DNF) |
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| 3/7/2020 | Smoky Mountain Speedway - Maryville, TN Tennessee Tipoff Dirt Super Late Models: World of Outlaws - Late Models Sportsmans, Dirt Crate Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 5th | - | 2nd | 15th |
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| 4/30/2020 | Tri-County Race Track - Brasstown, NC SCHAEFFER'S OIL TARHEEL INVITATIONAL PRESENTED BY PITSTOPUSA.COM! Dirt Super Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 10th |
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| 5/7/2020 | Senoia Raceway - Senoia, GA DirtonDirt.com Shootout Dirt Super Late Models, Dirt Crate Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 24th |
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| 5/15/2020 | Magnolia Motor Speedway - Columbus, MS Magnolia Mayhem 40 Dirt Super Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 4th |
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| 5/22/2020 | Jackson Motorplex - Jackson, MN WORLD OF OUTLAWS - Late Models 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models: Tri-State Late Models 305 Sprints - Winged | Results | | Ashton Winger (Dirt Super Late Models) | 4th | - | - | 9th |
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| 5/23/2020 | Jackson Motorplex - Jackson, MN WORLD OF OUTLAWS- Late Models Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models: Tri-State Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 2nd | - | - | 15th |
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| 5/29/2020 | Davenport Speedway - Davenport, IA Morton Buildings World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 7th | - | 5th | 17th |
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| 5/30/2020 | Davenport Speedway - Davenport, IA Morton Buildings World of Outlaws Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 1st | - | - | 18th |
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| 6/4/2020 | Eldora Speedway - Rossburg, OH Dirt Late Model Stream Dirt Super Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 7th | - | 7th | - |
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| 6/5/2020 | Eldora Speedway - Rossburg, OH Dirt Late Model Stream Dirt Super Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 4th | - | - | 16th |
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| 6/6/2020 | Eldora Speedway - Rossburg, OH Dirt Late Model Stream Dirt Super Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 9th | - | 10th | - |
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| 6/12/2020 | Deep South Speedway - Loxley, AL Dirt Super Late Models: Southern All Stars | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 6th |
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| 6/13/2020 | Deep South Speedway - Loxley, AL Dirt Super Late Models: Southern All Stars | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 1st |
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| 6/19/2020 | Volunteer Speedway - Bulls Gap, TN World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 4th | - | - | 4th |
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| 6/20/2020 | Volunteer Speedway - Bulls Gap, TN World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models Dirt Crate Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | - | - | 6th |
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| 6/25/2020 | Lernerville Speedway - Sarver, PA Firecracker Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | - | - | 7th |
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| 6/26/2020 | Lernerville Speedway - Sarver, PA Firecracker Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series | Results | | Ashton Winger (Dirt Super Late Models) | 10th (DNF) | - | 5th | 16th |
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| 6/27/2020 | Lernerville Speedway - Sarver, PA Firecracker 100 Dirt Super Late Models: World of Outlaws - Late Models RUSH Late Models: RUSH Late Model Series | Results | | Ashton Winger (Dirt Super Late Models) | 4th | - | - | 9th |
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| 7/2/2020 | Cedar Lake Speedway - New Richmond, WI FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Dirt Super Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 9th |
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| 7/3/2020 | Cedar Lake Speedway - New Richmond, WI FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 2nd | - | - | 1st |
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| 7/4/2020 | Cedar Lake Speedway - New Richmond, WI 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | - | - | 10th |
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| 7/10/2020 | Outagamie Speedway - Seymour, WI World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models IMCA Modified, IMCA Stock Car | Results | | Ashton Winger (Dirt Super Late Models) | 1st | - | - | 15th |
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| 7/11/2020 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 4th | - | - | 8th |
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| 7/14/2020 | Gondik Law Speedway - Superior, WI World of Outlaws Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Midwest Mods, WISSOTA Hornet | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | - | - | 5th |
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| 7/18/2020 | Red River Valley Speedway - West Fargo, ND World of Outlaw Late Models Dirt Super Late Models: World of Outlaws - Late Models Sprint Cars, Stock Cars, B Modifieds, Dirt Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 2nd | - | - | 5th |
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| 7/19/2020 | River Cities Speedway - Grand Forks, ND Dirt Super Late Models: World of Outlaws - Late Models B Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | - | - | 10th |
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| 7/25/2020 | Federated Auto Parts I-55 Raceway - Pevely, MO Old Timer's Night DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, DIRTcar Sport Compact, B Modifieds | Results | | Ashton Winger (DIRTcar Late Models) | 2nd | - | - | 1st |
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| 7/28/2020 | Davenport Speedway - Davenport, IA World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models B Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | 2nd | - | - | 14th |
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| 7/31/2020 | Kokomo Speedway - Kokomo, IN World Of Outlaws Morton Buildings Late Model Series Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 11th |
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| 8/4/2020 | Beaver Dam Raceway - Beaver Dam, WI World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models Semi-Pro Legends | Results | | Ashton Winger (Dirt Super Late Models) | 5th | - | 1st | 8th |
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| 8/6/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models USRA Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 11th (DNF) | - | 11th (DNF) | 12th |
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| 8/7/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds, Dirt Late Models, USRA Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | 3rd | 4th | - | - |
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| 8/8/2020 | Cedar Lake Speedway - New Richmond, WI USA Nationals Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models, USRA Modifieds | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 27th (DNF) |
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| 8/20/2020 | Lincoln Speedway - Abbottstown, PA | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 6th |
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| 8/21/2020 | Williams Grove Speedway - Mechanicsburg, PA World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models 410 Sprints - Winged | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 6th |
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| 8/22/2020 | Eriez Speedway - Erie, PA World of Outlaws Super Late Models, Vogt Memorial Econo-Mod Race $1000 to win Dirt Super Late Models, B Modifieds, Sport Compact | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | - |
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| 9/4/2020 | Lavonia Speedway - Lavonia, GA | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 13th |
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| 9/5/2020 | Lancaster Motor Speedway - Lancaster, SC World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 8th |
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| 9/10/2020 | Eldora Speedway - Rossburg, OH 2020 Intercontinental Classic Dirt Super Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | 10th | - |
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| 9/11/2020 | Eldora Speedway - Rossburg, OH 2020 Intercontinental Classic Dirt Super Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | DNS | - |
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| 9/15/2020 | Fairbury Speedway - Fairbury, IL "One for the Road" Late Model Special DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Ashton Winger (DIRTcar Late Models) | 4th | - | - | 16th (DNF) |
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| 9/25/2020 | Outlaw Speedway - Dundee, NY World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 8th |
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| 9/26/2020 | Thunder Mountain Speedway - Brookville, PA World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 3rd |
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| 10/2/2020 | Cherokee Speedway - Gaffney, SC World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 19th |
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| 10/3/2020 | 411 Motor Speedway - Seymour, TN World of Outlaws Morton Buildings Late Models Dirt Super Late Models: World of Outlaws - Late Models Sportsmans, A Modifieds, Street Stocks, Vintage Modifieds, Dirt Crate Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 11th |
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| 10/16/2020 | Smoky Mountain Speedway - Maryville, TN King off the Mountain "All Star Championship" Weekend Dirt Super Late Models, Dirt Crate Late Models, 604 Crate Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | - |
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| 10/17/2020 | Smoky Mountain Speedway - Maryville, TN King off the Mountain "All Star Championship" Weekend Night 2 Dirt Super Late Models, Sportsmans, 604 Crate Late Models | Results | | Ashton Winger (Dirt Super Late Models) | 1st | - | - | 17th |
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| 10/24/2020 | Whynot Motorsports Park - Meridian, MS Dirt Super Late Models, Dirt Late Models | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | DNS |
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| 11/4/2020 | The Dirt Track at Charlotte - Concord, NC | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 18th |
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| 11/5/2020 | The Dirt Track at Charlotte - Concord, NC Can-Am World Finals Dirt Super Late Models: World of Outlaws - Late Models DIRTcar Big Block Modifieds: Super DIRTCar Series | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 17th |
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| 11/21/2020 | Senoia Raceway - Senoia, GA | Results | | Ashton Winger (Dirt Super Late Models) | - | - | - | 4th |
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