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| 5/10/2019 | 300 Raceway - Farley, IA Opening Night presented by Cen-Pe-Co Lubricants A Modifieds, B Modifieds, IMCA Late Models | Results | | David Webster (IMCA Late Models) | 6th | - | - | 8th |
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| 5/12/2019 | Dubuque Fairgrounds Speedway - Dubuque, IA Mother's Day Salute - Weekly Racing Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 7th | - | - | 11th |
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| 6/27/2019 | Benton County Speedway - Vinton, IA IMCA Late Models: Deery Brothers Summer Series Hobby Stocks, Stock Cars, B Modifieds, 600cc Modifieds, Sport Compact | Results | | David Webster (IMCA Late Models) | DNS | - | - | 26th |
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| 7/7/2019 | Dubuque Fairgrounds Speedway - Dubuque, IA Weekly Racing Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Economy Late Models, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 6th | - | - | 12th |
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| 7/21/2019 | Dubuque Fairgrounds Speedway - Dubuque, IA Eichman's Bar & Grill Late Model Season Championship - Weekly Racing Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Economy Late Models, IMCA Late Models, Sport Compact | Results | | David Webster (Economy Late Models) | 1st | - | - | 3rd |
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| 7/28/2019 | Dubuque Fairgrounds Speedway - Dubuque, IA Julien Dubuque Classic Fair Race Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Vintage Full Body Stock Cars, Vintage Modifieds, IMCA Late Models, Sport Compact | Results | | David Webster (IMCA Late Models) | 6th | - | - | 10th |
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| 8/4/2019 | Dubuque Fairgrounds Speedway - Dubuque, IA Weekly Racing Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Economy Late Models, Sport Compact | Results | | David Webster (Economy Late Models) | 4th | - | - | 2nd |
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| 8/7/2019 | 300 Raceway - Farley, IA Cen-pe-co Lubricants Wednesday Night Racing Stock Cars, A Modifieds, B Modifieds, IMCA Late Models | Results | | David Webster (IMCA Late Models) | 8th | - | - | 8th |
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| 8/21/2019 | 300 Raceway - Farley, IA 42nd Annual Yankee Dirt Track Classic Dirt Super Late Models, Stock Cars, A Modifieds, B Modifieds, Generic 1 | Results | | David Webster (Generic 1) | - | - | - | - |
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| 8/22/2019 | 300 Raceway - Farley, IA 42nd Annual Yankee Dirt Track Classic Dirt Super Late Models: SLMR Late Model Series Stock Cars, A Modifieds, B Modifieds | Results | | David Webster (Dirt Super Late Models) | 7th | - | 10th | - |
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| 8/23/2019 | 300 Raceway - Farley, IA 42nd Annual Yankee Dirt Track Classic Dirt Super Late Models: SLMR Late Model Series Stock Cars, A Modifieds, B Modifieds | Results | | David Webster (Dirt Super Late Models) | 9th | - | DNS | - |
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| 8/24/2019 | West Liberty Raceway - West Liberty, IA IMCA Late Models: Deery Brothers Summer Series | Results | | David Webster (IMCA Late Models) | 8th | - | 14th | 23rd |
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| 9/12/2019 | Knoxville Raceway - Knoxville, IA Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | David Webster (Dirt Super Late Models) | 8th | - | 15th | - |
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| 9/13/2019 | Knoxville Raceway - Knoxville, IA Dirt Super Late Models: Lucas Oil Late Model Dirt Series | Results | | David Webster (Dirt Super Late Models) | 9th | - | 16th | - |
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| 9/26/2019 | 141 Speedway - Maribel, WI 10th Annual Creek Classic Practice Night Dirt Late Models: Dirt Kings Late Model Tour | Results | | David Webster (Dirt Late Models) | 8th | - | - | 24th |
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| 10/19/2019 | Peoria Speedway - Peoria, IL Midgets, DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Hornets | Results | | David Webster (DIRTcar Late Models) | 6th | - | 2nd | 18th |
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