| | Heat | Dash | B Feature | A Feature |
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| 7/10/2020 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Chad Baldwin (Winged Outlaw) | 3rd | - | - | 5th |
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| 7/11/2020 | Macon Speedway - Macon, IL Fireman's Ball & First Responders Night / Sportsman Topless 40 and CEFCU Kids Club DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Chad Baldwin (Winged A-Class) | 1st | - | - | 8th |
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| 7/18/2020 | Macon Speedway - Macon, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Chad Baldwin (Winged A-Class) | 4th | - | - | 15th (DNF) |
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| 8/8/2020 | Macon Speedway - Macon, IL Regular Night of Racing at Mighty Macon Speedway DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Chad Baldwin (Winged A-Class) | 1st | - | - | 19th |
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| 8/15/2020 | Macon Speedway - Macon, IL Eve of Destruction VI with FIREWORKS & Diane Bennett Memorial DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Chad Baldwin (Winged A-Class) | 4th | - | - | 6th |
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| 8/21/2020 | Lincoln Speedway - Lincoln, IL NIght Before State Fair Race Midgets: POWRi Economy Midgets, DIRTcar UMP Modifieds, Winged Outlaw, Pro Late Model | Results | | Chad Baldwin (Winged Outlaw) | 7th | - | - | 15th |
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| 8/23/2020 | Jacksonville Speedway - Jacksonville, IL POWRi Midgets and Micros at Jacksonville Speedway Midgets: POWRi Winged Outlaw | Results | | Chad Baldwin (Winged Outlaw) | 6th | - | 8th | - |
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