| | Heat | Dash | B Feature | A Feature |
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| 5/1/2021 | Plymouth Speedway - Plymouth, IN Cabin Fever - Season Opener DIRTcar UMP Modifieds, Asphalt Mini Stocks, Super Sports, Stock Non-Wing, Street Stocks | Results | | Timothy Bennett (DIRTcar UMP Modifieds) | 6th | - | - | - |
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| 5/29/2021 | Fairbury Speedway - Fairbury, IL FALS Cup Weekly Racing, Earl J Hubert Memorial Street Stock Special DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, Street Stocks, Pro Late Model | Results | | Timothy Bennett (DIRTcar UMP Modifieds) | 9th | - | 7th | - |
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| 6/17/2021 | Kankakee County Speedway - Kankakee, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Timothy Bennett (DIRTcar UMP Modifieds) | 8th | - | 4th | 13th |
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| 9/4/2021 | US 24 Speedway - Logansport, IN 3rd Annual Paul Moyer Mem. Outlaw NW $1000 to win, Rest. NW $300 to win point night 9 Non-Wing Outlaw, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints, Generic 1, Senior Micros | Results | | Timothy Bennett (Winged A-Class) | 9th | - | - | 16th |
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| 9/25/2021 | US 24 Speedway - Logansport, IN USAC Speed2 Thunder Midgets + reg. program Rest. run NW point night 11 Economy Midgets, Non-Wing Outlaw, Restricted Non Winged Micros, Winged A-Class, Stock Non-Wing, Junior Sprints, Senior Micros | Results | | Timothy Bennett (Winged A-Class) | 6th | - | - | 18th |
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