| | Heat | Dash | B Feature | A Feature |
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| 4/16/2021 | Tri City Speedway - Granite City, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw | Results | | Cliff Powell (Winged Outlaw) | 5th | - | - | DNS |
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| 5/1/2021 | Macon Speedway - Macon, IL CEFCU Kid's Club Regular Night of Racing DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Cliff Powell (Winged A-Class) | 7th | - | - | 16th |
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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 | | Cliff Powell (Winged A-Class) | 3rd | - | - | 12th |
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| 6/4/2021 | Tri City Speedway - Granite City, IL "4-Cyl Takeover" LM, Mods, BMods, St Stk, Wing Micros $500, 4-cyl $1000,$800,$600 + Kids Power Wheel DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Winged Outlaw, B Modifieds, Street Stocks | Results | | Cliff Powell (Winged Outlaw) | 5th | - | - | 9th |
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| 8/14/2021 | Macon Speedway - Macon, IL HART Non Wing Micros DIRTcar UMP Modifieds, Non-Wing Outlaw, Stock Non-Wing, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Cliff Powell (Non-Wing Outlaw) | 6th | - | - | 14th |
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| 9/1/2021 | Wayne County Speedway - Wayne City, IL DuQuoin State Fair Midgets, Non-Wing Outlaw, Restricted 'A' Class | Results | | Cliff Powell (Non-Wing Outlaw) | 6th | - | - | 16th |
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| 9/12/2021 | Avcom Park Speedway - Avon, IL Push & Pray Hideaway Night Non-Wing Outlaw, Dirt Cage Kart Junior 1, Flat Adult Clone, Restricted Box Stock, Unrestricted Box Stock, 250 Winged Outlaw, 500 Winged Open Outlaw, Pony Stock, Flat Jr. 1 Clone, Predator Maxxis | Results | | Cliff Powell (Non-Wing Outlaw) | 1st | - | - | - |
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