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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 | | Sean Rupp (A Modifieds) | 4th | - | - | 9th |
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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 | | Sean Rupp (IMCA Modified) | 3rd | - | - | 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 | | Sean Rupp (A Modifieds) | 3rd | - | - | 14th |
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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 | | Sean Rupp (A Modifieds) | 3rd | - | - | 6th |
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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 | | Sean Rupp (IMCA Modified) | 2nd | - | - | 6th |
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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 | | Sean Rupp (A Modifieds) | 4th | - | - | 11th |
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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 | | Sean Rupp (IMCA Modified) | 3rd | - | - | 9th |
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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 | | Sean Rupp (A Modifieds) | 5th | - | - | 5th |
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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 | | Sean Rupp (IMCA Modified) | 1st | - | - | 7th |
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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 | | Sean Rupp (A Modifieds) | 6th | - | - | 16th |
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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 | | Sean Rupp (IMCA Modified) | 5th | - | - | 14th |
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| 7/11/2021 | Dubuque Fairgrounds Speedway - Dubuque, IA DGaul Farms Weekly Racing Hobby Stocks, A Modifieds, B Modifieds, Semi-Pro Legends, IMCA Late Models, Dirt Mini Late Models | Results | | Sean Rupp (A Modifieds) | 8th | - | - | 5th |
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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 | | Sean Rupp (IMCA Modified) | 7th | - | - | 15th |
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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 | | Sean Rupp (A Modifieds) | 4th | - | - | 9th |
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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 | | Sean Rupp (IMCA Modified) | 4th | - | - | 3rd |
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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 | | Sean Rupp (A Modifieds) | 7th | - | - | 10th |
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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 | | Sean Rupp (A Modifieds) | 8th | - | - | 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 | | Sean Rupp (IMCA Modified) | 7th | - | - | 9th |
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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 | | Sean Rupp (A Modifieds) | 7th | - | - | 12th |
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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 | | Sean Rupp (IMCA Modified) | 3rd | - | - | 11th |
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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 | | Sean Rupp (A Modifieds) | 7th | - | - | 7th |
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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 | | Sean Rupp (A Modifieds) | 3rd | - | - | 4th |
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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 | | Sean Rupp (IMCA Modified) | 6th | - | - | 9th |
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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 | | Sean Rupp (B Modifieds) | 2nd | - | - | 8th |
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| 9/30/2021 | Cedar County Raceway - Tipton, IA Hoker Trucking Darkside Fall Bash IMCA Late Models, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Sean Rupp (IMCA Modified) | 8th | - | DNS | - |
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| 10/2/2021 | Cedar County Raceway - Tipton, IA Hoker Trucking Darkside Fall Bash Street Stocks, Vintage Full Body Stock Cars, Super Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock | Results | | Sean Rupp (IMCA Modified) | 8th | - | DNS | - |
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