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| 4/24/2021 | Off Road Speedway - Norfolk, NE North-South Challenge $1,500 to win Dirt Late Models: Tri-State Late Models Hobby Stocks, Stock Cars, B Modifieds, Pro Late Model | Results | | Mike Benson (Dirt Late Models) | 4th | - | - | 19th |
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| 5/22/2021 | Off Road Speedway - Norfolk, NE Rumble at the Ranch - MSTS at Off Road Speedway 360 Sprints - Winged: Midwest Sprint Touring Series Dirt Super Late Models: SLMR Late Model Series Hobby Stocks, Stock Cars, B Modifieds | Results | | Mike Benson (Dirt Super Late Models) | 7th | - | 7th | - |
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| 5/31/2021 | Huset's Speedway - Brandon, SD NOSA Sprint Cars $7500 to win / Tri-State Late Models - Ben Nothdurft Memorial $6,000 to win 410 Sprints - Winged: Northern Outlaw Sprint Association Dirt Late Models: Tri-State Late Models WISSOTA Late Model | Results | | Mike Benson (Dirt Late Models) | 6th | - | 7th | - |
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| 6/11/2021 | Rapid Speedway - Rock Rapids, IA $1,500 to win at Rapid Speedway Dirt Late Models: Tri-State Late Models DIRTcar Sportsmans, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars | Results | | Mike Benson (Dirt Late Models) | 4th | - | - | 13th |
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| 7/9/2021 | Jackson Motorplex - Jackson, MN World of Outlaws Morton Buildings Late Model Series Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models: Tri-State Late Models | Results | | Mike Benson (Dirt Late Models) | 7th | - | - | 7th |
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| 7/10/2021 | Jackson Motorplex - Jackson, MN World of Outlaws Morton Buildings Late Model Series Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models: Tri-State Late Models | Results | | Mike Benson (Dirt Late Models) | 4th | - | - | 10th |
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| 7/20/2021 | Rapid Speedway - Rock Rapids, IA Lyon County Fair Races 360 Sprints - Winged: Midwest Sprint Touring Series Dirt Late Models: Tri-State Late Models A Modifieds | Results | | Mike Benson (Dirt Late Models) | 6th | - | - | 15th |
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| 7/24/2021 | I-90 Speedway - Hartford, SD Dirt Late Models: Tri-State Late Models 305 Sprints - Winged, Street Stocks, USRA B-Mods, USRA Hobby Stocks | Results | | Mike Benson (Dirt Late Models) | 7th | - | - | 15th |
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| 8/13/2021 | Rapid Speedway - Rock Rapids, IA $1,500 to win at Rapid Speedway Dirt Late Models: Tri-State Late Models DIRTcar Sportsmans, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars | Results | | Mike Benson (Dirt Late Models) | 4th | - | - | 14th |
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| 8/14/2021 | Park Jefferson International Speedway - Jefferson, SD I State Truck Center IMCA Championship plus $2,000 to win Tri-State Late Models by Zeitner & Sons Dirt Late Models: Tri-State Late Models Hobby Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock | Results | | Mike Benson (Dirt Late Models) | 6th | - | - | 5th |
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| 9/3/2021 | Interstate Speedway (SD) - Jefferson, SD Agrivision Equipment Night Dirt Late Models: Tri-State Late Models IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Mike Benson (Dirt Late Models) | 4th | - | - | 13th |
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| 9/4/2021 | I-90 Speedway - Hartford, SD Dirt Late Models: Tri-State Late Models Street Stocks, USRA B-Mods, USRA Hobby Stocks | Results | | Mike Benson (Dirt Late Models) | 6th | - | - | 17th |
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| 9/5/2021 | Interstate Speedway (SD) - Jefferson, SD IMCA Weekly Racing Dirt Late Models: Tri-State Late Models IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Mike Benson (Dirt Late Models) | 4th | - | - | 13th |
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| 9/14/2021 | Clay County Fair Speedway - Spencer, IA Clay County Fair $2,000 to win [PREMIER EVENT] 360 Sprints - Winged: ASCS National Dirt Late Models: Tri-State Late Models 410 Sprints - Winged, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Mike Benson (Dirt Late Models) | 4th | - | - | 16th |
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| 9/18/2021 | Rapid Speedway - Rock Rapids, IA $1,500 to win Rapid Nationals 360 Sprints - Winged: Midwest Sprint Touring Series Dirt Late Models: Tri-State Late Models DIRTcar Sportsmans, USRA B-Mods | Results | | Mike Benson (Dirt Late Models) | 7th | - | - | 11th |
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| 9/24/2021 | Huset's Speedway - Brandon, SD C & B Operations Cheater's Night / Tri-State Late Models Dirt Late Models: Tri-State Late Models Hobby Stocks, B Modifieds, Street Stocks | Results | | Mike Benson (Dirt Late Models) | 6th | - | - | 16th |
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| 9/25/2021 | Fairmont Raceway - Fairmont, MN Fairmont Raceway Dirt Late Models: Tri-State Late Models Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Mike Benson (Dirt Late Models) | 4th | - | - | 9th |
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| 10/9/2021 | Murray County Speedway - Slayton, MN Hub City Rumble - Repairable Vehicles.com Tri State Late Models Dirt Late Models: Tri-State Late Models Factory Stocks, Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Mike Benson (Dirt Late Models) | 5th | - | - | 13th |
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