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| 4/17/2021 | Hamilton County Speedway - Webster City, IA Malvern Bank $3,000-to-Win Late Models Dirt Super Late Models: SLMR Late Model Series USRA B-Mods, USRA Modifieds, USRA Hobby Stocks, USRA Stock Cars, USRA Tuners | Results | | Jesse Olson (USRA Stock Cars) | 4th | - | - | 22nd (DNF) |
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| 4/30/2021 | Rapid Speedway - Rock Rapids, IA Weekly Racing Series + 305 Sprints DIRTcar Sportsmans, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars, IMCA RaceSaver Sprint Car | Results | | Jesse Olson (USRA Stock Cars) | 2nd | - | - | 8th |
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| 5/7/2021 | Rapid Speedway - Rock Rapids, IA Rapid Speedway - WEST Dirt Super Late Models: SLMR Late Model Series DIRTcar Sportsmans, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars | Results | | Jesse Olson (USRA Stock Cars) | 3rd | - | - | 8th |
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| 5/15/2021 | Hamilton County Speedway - Webster City, IA Kid's Night + $1,000-to-Win Mods USRA B-Mods, USRA Modifieds, USRA Hobby Stocks, USRA Stock Cars, USRA Tuners | Results | | Jesse Olson (USRA Stock Cars) | 2nd | - | - | 16th |
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| 5/21/2021 | Rapid Speedway - Rock Rapids, IA Weekly Racing Series + 360 Sprints 360 Sprints - Winged: Midwest Sprint Touring Series DIRTcar Sportsmans, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars | Results | | Jesse Olson (USRA Stock Cars) | 6th | - | 8th (DNF) | - |
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| 5/29/2021 | Deer Creek Speedway - Spring Valley, MN 18th Annual USMTS Southern MN Spring Challenge A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, USRA Stock Cars, WISSOTA Midwest Mods | Results | | Jesse Olson (USRA Stock Cars) | 6th | - | - | 15th |
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| 6/13/2021 | Mason City Motor Speedway - Mason City, IA Season Opener USRA B-Mods, USRA Modifieds, USRA Hobby Stocks, USRA Stock Cars, USRA Tuners | Results | | Jesse Olson (USRA Stock Cars) | 7th | - | - | 19th |
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| 6/24/2021 | Princeton Speedway - Princeton, MN Siercks Memorial Hobby Stocks, A Modifieds, B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Jesse Olson (IMCA Stock Car) | - | - | - | - |
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| 7/16/2021 | Fairmont Raceway - Fairmont, MN Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Jesse Olson (Stock Cars) | 1st | - | - | 6th (DNF) |
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| 7/17/2021 | Worthington Speedway - Worthington, MN Regular Night Hobby Stocks, Stock Cars, Sportsmans, A Modifieds, B Modifieds, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Jesse Olson (Stock Cars) | 3rd | - | - | 4th |
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| 7/21/2021 | 141 Speedway - Maribel, WI King of the Creek IV $10,000.00 to Win IMCA Stock Cars - Qualifying Sport Compact, IMCA Modified, IMCA Stock Car | Results | | Jesse Olson (IMCA Stock Car) | 10th | - | - | 79th |
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| 7/22/2021 | 141 Speedway - Maribel, WI King of the Creek IV $10,000.00 to Win IMCA Stock Cars Stock Cars, IMCA Northern SportMod, IMCA Stock Car | Results | | Jesse Olson (IMCA Stock Car) | 8th | - | - | - |
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| 7/31/2021 | Worthington Speedway - Worthington, MN Regular Night Hobby Stocks, Stock Cars, Sportsmans, A Modifieds, B Modifieds, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Jesse Olson (Stock Cars) | 1st | - | - | 7th |
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| 8/6/2021 | Murray County Speedway - Slayton, MN Regular Night - Sponsored by Van't Hof Milk Hauling Factory Stocks, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Jesse Olson (Stock Cars) | 5th | - | - | 5th |
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| 8/13/2021 | Murray County Speedway - Slayton, MN Jerry "Mahoney" Gronewold Hobby Special, plus Vintage Race Shirt Night Factory Stocks, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Jesse Olson (Stock Cars) | 5th | - | - | 5th |
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| 8/14/2021 | Worthington Speedway - Worthington, MN Regular Night Hobby Stocks, Stock Cars, Sportsmans, A Modifieds, B Modifieds, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Jesse Olson (Stock Cars) | 1st | - | - | 11th (DNF) |
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| 8/16/2021 | Fairmont Raceway - Fairmont, MN FAIR RACE #1 Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Jesse Olson (Stock Cars) | 5th | - | - | 7th |
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| 8/21/2021 | Worthington Speedway - Worthington, MN Regular Night Hobby Stocks, Stock Cars, Sportsmans, A Modifieds, B Modifieds, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Jesse Olson (Stock Cars) | 4th | - | - | 17th (DNF) |
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| 9/4/2021 | Deer Creek Speedway - Spring Valley, MN 16th Annual USMTS Labor Day Duel A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, USRA Late Models, USRA Stock Cars | Results | | Jesse Olson (USRA Stock Cars) | 5th | - | - | 21st |
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| 9/18/2021 | Deer Creek Speedway - Spring Valley, MN Stock Car Nationals USRA Hobby Stocks, USRA Stock Cars | Results | | Jesse Olson (USRA Stock Cars) | 8th (DNF) | - | 13th (DNF) | - |
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| 9/19/2021 | Worthington Speedway - Worthington, MN King Turkey Day Races Hobby Stocks, Stock Cars, Sportsmans, A Modifieds, B Modifieds, Sport Compact | Results | | Jesse Olson (Stock Cars) | DNS | - | - | DNS |
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| 10/6/2021 | Lucas Oil Speedway - Wheatland, MO Practice Night USRA Stock Cars: USRA Nationals USRA B-Mods, USRA Modifieds, USRA Hobby Stocks, USRA Tuners | Results | | Jesse Olson (USRA Stock Cars) | - | - | - | - |
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| 10/12/2021 | Batesville Motor Speedway - Locust Grove, AR World IMCA Stock Car Championship Practice IMCA Stock Car | Results | | Jesse Olson (IMCA Stock Car) | - | - | - | - |
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