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| 5/14/2021 | Lafayette County Speedway - Darlington, WI Weekly Racing Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | Jeff Bennett (IMCA Hobby Stock) | 4th | - | - | 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 | | Jeff Bennett (Hobby Stocks) | 7th | - | - | 11th |
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| 6/6/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, IMCA Late Models, Sport Compact, Dirt Mini Late Models | Results | | Jeff Bennett (Hobby Stocks) | 7th | - | - | 15th |
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| 6/11/2021 | Lafayette County Speedway - Darlington, WI Weekly Racing/Canoe Fest Weekend/Kids Night/Bike Giveaway Economy Late Models, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Hobby Stock | Results | | Jeff Bennett (IMCA Hobby Stock) | 5th | - | - | 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 | | Jeff Bennett (Hobby Stocks) | 4th | - | - | 11th |
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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 | | Jeff Bennett (IMCA Hobby Stock) | 3rd | - | - | 4th |
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| 7/28/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Sprint Invaders - Dubuque Fairgrounds Speedway 360 Sprints - Winged: Sprint Invaders Hobby Stocks, A Modifieds, B Modifieds, Sport Compact | Results | | Jeff Bennett (Hobby Stocks) | 6th | - | - | 20th |
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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 | | Jeff Bennett (Hobby Stocks) | 4th | - | - | 12th |
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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 | | Jeff Bennett (IMCA Hobby Stock) | 3rd | - | - | 10th |
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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 | | Jeff Bennett (Hobby Stocks) | 4th | - | - | 5th |
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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 | | Jeff Bennett (IMCA Hobby Stock) | 6th | - | - | 19th |
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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 | | Jeff Bennett (Hobby Stocks) | 5th | - | - | 18th |
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| 9/23/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Dubuque Speedway - EAST Dirt Super Late Models: SLMR Late Model Series Hobby Stocks, A Modifieds, B Modifieds, Vintage Full Body Stock Cars, Vintage Modifieds | Results | | Jeff Bennett (Hobby Stocks) | 4th | - | - | 7th |
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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 | | Jeff Bennett (Hobby Stocks) | 6th | - | - | 15th |
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| 10/15/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Iowa Dirt Nationals Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Semi-Pro Legends, Sport Compact, IMCA Modified | Results | | Jeff Bennett (Hobby Stocks) | 8th | - | 5th | 24th |
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| 10/16/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA Iowa Dirt Nationals Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, 600cc Modifieds, Sport Compact, IMCA Modified | Results | | Jeff Bennett (Hobby Stocks) | 6th | - | - | 18th |
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