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| 5/1/2020 | Mississippi Thunder Speedway - Fountain City, WI Weekly Racing Dirt Late Models, USRA B-Mods, USRA Modifieds, USRA Late Models, USRA Hobby Stocks | Results | | David Webster (Dirt Late Models) | 7th | - | - | 14th |
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| 5/22/2020 | Mississippi Thunder Speedway - Fountain City, WI USMTS Spring Shootout and Rumble by the River 40 Presented by Coca-Cola A Modifieds: USMTS - United States Modified Touring Series Dirt Late Models, USRA B-Mods, USRA Modifieds, USRA Hobby Stocks | Results | | David Webster (Dirt Late Models) | 8th | - | 10th | - |
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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 | | David Webster (Dirt Super Late Models) | 8th | - | 8th (DNF) | - |
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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 | | David Webster (Dirt Super Late Models) | 8th | - | 7th | - |
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| 5/31/2020 | Dubuque Fairgrounds Speedway - Dubuque, IA IMCA Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 7th | - | - | 15th |
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| 6/5/2020 | 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) | 3rd | - | - | 3rd |
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| 6/7/2020 | Dubuque Fairgrounds Speedway - Dubuque, IA IMCA Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, Semi-Pro Legends, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 3rd | - | - | 11th |
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| 6/12/2020 | 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) | 7th | - | - | DNS |
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| 6/13/2020 | Maquoketa Speedway - Maquoketa, IA MLRA Late Models Inaugural Event Dirt Super Late Models: Lucas Oil MLRA Vintage Full Body Stock Cars, IMCA Modified, IMCA Northern SportMod, IMCA Sport Compact | Results | | David Webster (Dirt Super Late Models) | 9th | - | 9th | - |
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| 6/14/2020 | West Liberty Raceway - West Liberty, IA Dirt Super Late Models: Lucas Oil MLRA | Results | | David Webster (Dirt Super Late Models) | 9th | - | 8th | - |
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| 6/21/2020 | Wilmot Raceway - Wilmot, WI DIRTcar Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals Dirt Late Models: Dirt Kings Late Model Tour Non Wing Crate Sprints: Wisconsin wingLESS Sprints A Modifieds, Street Stocks | Results | | David Webster (DIRTcar Late Models) | - | - | - | - | | David Webster (Dirt Late Models) | 6th | - | - | 16th |
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| 6/24/2020 | Lucas Oil Speedway - Wheatland, MO MLRA Mid-Week Mayhem, plus Midwest Mods Dirt Super Late Models: Lucas Oil MLRA Midwest Modifieds, Pro Late Model | Results | | David Webster (Dirt Super Late Models) | 6th | - | 8th | - |
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| 6/28/2020 | Dubuque Fairgrounds Speedway - Dubuque, IA IMCA Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 4th | - | - | 9th |
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| 7/5/2020 | Dubuque Fairgrounds Speedway - Dubuque, IA IMCA Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, Masters Legends, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 6th | - | - | 8th |
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| 7/10/2020 | Lafayette County Speedway - Darlington, WI Armed Forces Night! Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 6th | - | - | 5th |
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| 7/12/2020 | Dubuque Fairgrounds Speedway - Dubuque, IA IMCA Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, Semi-Pro Legends, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 6th | - | - | 5th |
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| 7/13/2020 | 300 Raceway - Farley, IA Lucas Oil Late Model Dirt Series 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) | 9th | - | 4th | 17th |
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| 7/17/2020 | Lafayette County Speedway - Darlington, WI Night 1, Lafyette County Speedway Double Header Masters 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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| 7/19/2020 | Dubuque Fairgrounds Speedway - Dubuque, IA IMCA Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 8th | - | - | 12th |
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| 7/22/2020 | Fayette County Speedway - West Union, IA 2020 Fayette County Fair Race - 1st Annual FCS Late Model Showdown - $4,000 to win/$400 to start! Dirt Late Models, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars | Results | | David Webster (Dirt Late Models) | 7th | - | - | 14th (DNF) |
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| 7/31/2020 | Lafayette County Speedway - Darlington, WI Weekly Racing! Masters Legends, Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 6th | - | - | 14th |
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| 8/2/2020 | Dubuque Fairgrounds Speedway - Dubuque, IA Julien Dubuque Classic Fair Races Hobby Stocks, A Modifieds, B Modifieds, Vintage Modifieds, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 6th | - | - | 21st |
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| 8/7/2020 | Lafayette County Speedway - Darlington, WI Weekly Racing! Masters Legends, Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 1st | - | - | 9th |
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| 8/12/2020 | 300 Raceway - Farley, IA Matthews Distributing Co. IMCA Weekly Racing Stock Cars, A Modifieds, B Modifieds, IMCA Late Models | Results | | David Webster (IMCA Late Models) | 7th | - | - | 13th |
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| 8/14/2020 | Lafayette County Speedway - Darlington, WI Weekly Racing! Masters Legends, Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 5th | - | - | 16th |
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| 8/21/2020 | Lafayette County Speedway - Darlington, WI Season Championship! Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 5th | - | - | 16th |
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| 9/18/2020 | Lafayette County Speedway - Darlington, WI Bob Larson Memorial Night 1 Vintage Full Body Stock Cars, Economy Late Models, IMCA Hobby Stock | Results | | David Webster (Economy Late Models) | 1st | - | - | 4th |
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| 9/19/2020 | Lafayette County Speedway - Darlington, WI Bob Larson Memorial Night 2 Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod | Results | | David Webster (Economy Late Models) | 3rd | - | - | 6th |
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| 10/15/2020 | Tri City Speedway - Granite City, IL Open Practice 6:30 pm - 9:00 pm for Lucas Oil MLRA Late Models, Modifieds and B Mods Dirt Super Late Models: Lucas Oil MLRA DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds | Results | | David Webster (Dirt Super Late Models) | - | - | - | - |
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| 10/16/2020 | Tri City Speedway - Granite City, IL Lucas Oil MLRA Late Models Night #1 $5000 to win plus UMP Modifieds $2000 to win Dirt Super Late Models: Lucas Oil MLRA DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | David Webster (Dirt Super Late Models) | 9th | - | 12th | - |
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| 10/17/2020 | Tri City Speedway - Granite City, IL Lucas Oil MLRA Late Models Night #2 $7000 to win with UMP Modifieds $2000 and B-Mods $1000 to win Dirt Super Late Models: Lucas Oil MLRA DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds | Results | | David Webster (Dirt Super Late Models) | 10th | - | 11th | - |
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