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| 4/30/2021 | Coles County Speedway - Mattoon, IL Opening Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Derek Bradshaw (Winged Outlaw) | 4th | - | - | 8th |
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| 5/14/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Derek Bradshaw (Winged Outlaw) | 5th | - | - | 8th |
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| 5/15/2021 | Macon Speedway - Macon, IL 95Q Armed Forces Night (Featuring Free Admission for Active and Retired Military DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Derek Bradshaw (Winged A-Class) | 7th | - | - | 11th |
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| 5/31/2021 | Macon Speedway - Macon, IL Memorial Day Twin 50s - SLM 50 laps & Modifieds 50 laps DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets | Results | | Derek Bradshaw (Winged A-Class) | 8th (DNF) | - | - | DNS |
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| 7/17/2021 | Macon Speedway - Macon, IL Church Night Featuring Faster Pastor Race DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model, Limited Modified | Results | | Derek Bradshaw (Winged A-Class) | 9th | - | - | DNS |
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| 7/23/2021 | Coles County Speedway - Mattoon, IL Non Wing Hart Series Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Derek Bradshaw (Non-Wing Outlaw) | 7th | - | - | 17th |
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| 7/31/2021 | US 24 Speedway - Logansport, IN Weekly Rest class trophy night Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Derek Bradshaw (Senior Micros) | DNS | - | - | DNS |
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| 8/21/2021 | US 24 Speedway - Logansport, IN USAC Speed2 Thunder Midgets, reg. program Hardy Hoagland Mem point night 7 Economy Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Derek Bradshaw (Senior Micros) | 7th | - | - | 15th |
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| 9/3/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Derek Bradshaw (Non-Wing Outlaw) | 3rd (DNF) | - | - | DNS |
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