| | Heat | Dash | B Feature | A Feature |
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| 4/21/2023 | Jacksonville Speedway - Jacksonville, IL Opening Night 410 Sprints - Winged, 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Jacob Stewart (Winged Outlaw) | 3rd | - | - | 4th |
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| 5/5/2023 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Jacob Stewart (Winged Outlaw) | 7th | - | - | 9th |
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| 5/6/2023 | Highland Speedway - Highland, IL Mowa Sprint Cars 410 Sprints - Winged: MOWA-Midwest Open Wheel Association DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Jacob Stewart (Winged Outlaw) | 6th | - | 7th | - |
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| 5/12/2023 | Jacksonville Speedway - Jacksonville, IL $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged, Winged Outlaw | Results | | Jacob Stewart (Winged Outlaw) | 5th | - | - | DNS |
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| 5/26/2023 | Macon Speedway - Macon, IL Cornfield Combat Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, HART Non-Wing Micros | Results | | Jacob Stewart (HART Non-Wing Micros) | 7th | - | - | - |
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| 5/27/2023 | Macon Speedway - Macon, IL Cornfield Combat with $5,000 to win Non Wing Micros Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, HART Non-Wing Micros | Results | | Jacob Stewart (HART Non-Wing Micros) | 12th (DNF) | - | - | - |
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| 6/16/2023 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Jacob Stewart (Winged Outlaw) | 4th | - | - | 5th |
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| 6/23/2023 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets 410 Sprints - Winged, Winged Outlaw, Street Stocks | Results | | Jacob Stewart (Winged Outlaw) | 3rd | - | - | 10th |
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