| | Heat | Dash | B Feature | A Feature |
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| 5/15/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Craig Usher (Winged Outlaw) | 6th | - | - | 8th |
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| 7/3/2021 | Wayne County Speedway - Wayne City, IL Season Opener Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Craig Usher (Winged Outlaw) | 10th | - | - | 18th |
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| 7/17/2021 | Southern Illinois Raceway - Marion, IL Ike Dealership JR Sprint Special/Rising Stars Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Craig Usher (Winged Outlaw) | 9th | - | - | 12th |
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| 8/7/2021 | Wayne County Speedway - Wayne City, IL Hyper NON-Wing Outlaws $1250 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Craig Usher (Winged Outlaw) | 10th | - | 9th | - |
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