| | Heat | Dash | B Feature | A Feature |
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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 | | Jacob Stewart (Winged A-Class) | 5th | - | - | 11th (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 | | Jacob Stewart (Winged A-Class) | 7th | - | - | 16th |
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| 8/23/2020 | Jacksonville Speedway - Jacksonville, IL POWRi Midgets and Micros at Jacksonville Speedway Midgets: POWRi Winged Outlaw | Results | | Jacob Stewart (Winged Outlaw) | 8th | - | 7th | - |
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| 9/11/2020 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi Winged Outlaw | Results | | Jacob Stewart (Winged Outlaw) | - | - | - | - |
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| 10/9/2020 | Jacksonville Speedway - Jacksonville, IL Ron Milton Race of Champions Midgets: POWRi 410 Sprints - Winged, Winged Outlaw | Results | | Jacob Stewart (Winged Outlaw) | 7th | - | 13th | - |
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