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| 3/19/2021 | Bristol Motor Speedway - Bristol, TN Bristol Dirt Nationals Dirt Super Late Models: XR Workin' Man Series DIRTcar UMP Modifieds | Results | | David Webster (Dirt Super Late Models) | 8th | - | 7th | - |
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| 3/20/2021 | Bristol Motor Speedway - Bristol, TN Bristol Dirt Nationals Dirt Super Late Models: XR Workin' Man Series DIRTcar UMP Modifieds, Stock Cars, A Modifieds, Hornets, IMCA Sport Compact, 604 Crate Late Models | Results | | David Webster (Dirt Super Late Models) | 10th | - | 9th | - |
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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 | | David Webster (Dirt Super Late Models) | - | - | - | - |
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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 | | David Webster (Dirt Super Late Models) | 7th | - | 9th | - |
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| 4/15/2021 | Davenport Speedway - Davenport, IA Annual Event Dirt Super Late Models: Lucas Oil MLRA | Results | | David Webster (Dirt Super Late Models) | 9th | - | 8th | - |
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| 4/23/2021 | Lafayette County Speedway - Darlington, WI Season Opener! Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 6th | - | - | 12th |
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| 4/30/2021 | Lafayette County Speedway - Darlington, WI Weekly Racing Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 1st | - | - | 11th |
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| 5/2/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Badger's 85th Season Opener Badger Midgets: Badger Midget Auto Racing Association Hobby Stocks, A Modifieds, B Modifieds, IMCA Late Models | Results | | David Webster (IMCA Late Models) | 7th | - | - | 13th |
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| 5/7/2021 | Lafayette County Speedway - Darlington, WI Weekly Racing Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 5th | - | - | 5th |
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| 5/9/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, IMCA Late Models, Sport Compact, Dirt Mini Late Models | Results | | David Webster (IMCA Late Models) | 7th | - | - | 13th |
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| 5/14/2021 | Davenport Speedway - Davenport, IA Annual Event Dirt Super Late Models: Lucas Oil MLRA | Results | | David Webster (Dirt Super Late Models) | 7th | - | 6th | - |
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| 5/16/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Weekly Racing Fan Appreciation Night Hobby Stocks, A Modifieds, B Modifieds, Semi-Pro Legends, Economy Late Models, IMCA Late Models | Results | | David Webster (Economy Late Models) | 1st | - | - | DNS |
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| 5/21/2021 | 300 Raceway - Farley, IA Truck Country 50 Dirt Super Late Models: Lucas Oil Late Model Dirt Series A Modifieds, B Modifieds, IMCA Modified | Results | | David Webster (Dirt Super Late Models) | 6th | - | 8th | - |
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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 | | David Webster (Dirt Super Late Models) | 10th | - | 13th | - |
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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 | | David Webster (Dirt Super Late Models) | 9th | - | 11th | - |
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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 | | David Webster (Dirt Super Late Models) | - | - | 11th (DNF) | - |
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| 5/30/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, Masters Legends, Economy Late Models, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 6th | - | - | 14th |
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| 6/4/2021 | Lafayette County Speedway - Darlington, WI Weekly Racing Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 3rd | - | - | 13th |
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| 6/13/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, Semi-Pro Legends, Economy Late Models, IMCA Late Models | Results | | David Webster (Economy Late Models) | 3rd | - | - | 2nd |
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| 6/18/2021 | Lafayette County Speedway - Darlington, WI Weekly Racing Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 1st | - | - | 1st |
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| 7/2/2021 | 300 Raceway - Farley, IA 2nd Annual Event Dirt Super Late Models: Lucas Oil MLRA Stock Cars, A Modifieds, B Modifieds | Results | | David Webster (Dirt Super Late Models) | 8th | - | - | 23rd (DNF) |
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| 7/4/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Very Good Chiropractic Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, Masters Legends, Economy Late Models, IMCA Late Models | Results | | David Webster (Economy Late Models) | 2nd | - | - | 1st |
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| 7/9/2021 | Lafayette County Speedway - Darlington, WI Weekly Racing with INEX Legends Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 1st | - | - | 6th |
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| 7/16/2021 | Lafayette County Speedway - Darlington, WI Lafayette County Fair Race with AIRS Vintage Full Body Stock Cars, Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 1st | - | - | 5th |
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| 7/18/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Link Hydraulics Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, Economy Late Models, IMCA Late Models, Sport Compact | Results | | David Webster (Economy Late Models) | 3rd | - | - | 3rd |
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| 7/23/2021 | Lafayette County Speedway - Darlington, WI Weekly Racing Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 6th | - | - | 9th |
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| 8/1/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Julien Dubuque Classic Fair Race Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, IMCA Late Models, Sport Compact, Dirt Mini Late Models | Results | | David Webster (IMCA Late Models) | 5th | - | - | 17th |
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| 8/4/2021 | 300 Raceway - Farley, IA Harris Golf Cars / Cen-Pe-Co Lubricants Weekly Racing Stock Cars, A Modifieds, B Modifieds, IMCA Late Models | Results | | David Webster (IMCA Late Models) | 4th | - | - | 11th |
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| 8/6/2021 | Lafayette County Speedway - Darlington, WI Season Championship! Open, Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 1st | - | - | 6th |
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| 8/15/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Drew Cook & Sons Excavating & CALCO Spray Coatings Back to School Night Hobby Stocks, A Modifieds, B Modifieds, Semi-Pro Legends, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 4th | - | - | 14th |
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| 8/18/2021 | Lafayette County Speedway - Darlington, WI Grant County Fair Race Vintage Full Body Stock Cars, Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 1st | - | - | 2nd |
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| 8/22/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA The Dubuque Advertiser Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, Economy Late Models, IMCA Late Models, Dirt Mini Late Models | Results | | David Webster (Economy Late Models) | 1st | - | - | 4th |
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| 8/29/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA McDermott Excavating Season Championship Night Hobby Stocks, A Modifieds, B Modifieds, Masters Legends, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 7th | - | - | 11th |
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| 9/4/2021 | 300 Raceway - Farley, IA 300 Raceway - The Yankee - EAST/WEST Dirt Super Late Models: SLMR Late Model Series Stock Cars, A Modifieds, B Modifieds | Results | | David Webster (Dirt Super Late Models) | 7th | - | 9th | - |
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| 9/17/2021 | Lafayette County Speedway - Darlington, WI Bob Larson Memorial, Night 1 Open, Vintage Full Body Stock Cars, Economy Late Models, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 2nd | - | - | 1st |
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| 9/18/2021 | Lafayette County Speedway - Darlington, WI Bob Larson Memorial, Night 2 Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 2nd | - | - | 5th |
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| 9/25/2021 | Davenport Speedway - Davenport, IA Davenport Speedway - EAST Dirt Super Late Models: SLMR Late Model Series | Results | | David Webster (Dirt Super Late Models) | 2nd | - | - | 19th |
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| 10/14/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Iowa Dirt Nationals Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, IMCA Late Models, IMCA Modified | Results | | David Webster (IMCA Late Models) | 6th | - | - | 10th |
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| 10/16/2021 | Tri City Speedway - Granite City, IL 2nd Annual Event Dirt Super Late Models: Lucas Oil MLRA DIRTcar UMP Modifieds, B Modifieds | Results | | David Webster (Dirt Super Late Models) | 6th | - | - | 16th |
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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 | | David Webster (Dirt Super Late Models) | 3rd | - | 1st | 14th |
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| 12/4/2021 | The Dome at America's Center - St. Louis, MO Midgets, Dirt Super Late Models, A Modifieds | Results | | David Webster (Dirt Super Late Models) | - | - | 7th | - |
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