| | Heat | Dash | B Feature | A Feature |
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| 4/15/2023 | Macon Speedway - Macon, IL POWRi Micros at Macon Speedway DIRTcar Sportsmans, Winged Outlaw, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Jacob Tipton (Winged Outlaw) | 2nd | - | - | 8th |
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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 Tipton (Winged Outlaw) | DNS | - | DNS | - |
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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 Tipton (Winged Outlaw) | 8th | - | - | DNS |
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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 Tipton (Winged Outlaw) | 1st | - | - | 3rd |
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| 7/15/2023 | Macon Speedway - Macon, IL POWRi Micros at Macon Speedway DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Jacob Tipton (Winged Outlaw) | DNS | - | - | DNS |
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| 8/12/2023 | Macon Speedway - Macon, IL Throwback Sprint Cars / CEFCU Kids Club Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Non-Winged Sprints, Pro Late Model, Limited Modified, Dirt 6-cyl Stock Cars | Results | | Jacob Tipton (Winged Outlaw) | 2nd | - | - | 5th |
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| 9/8/2023 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged, 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Jacob Tipton (Winged Outlaw) | 2nd | - | - | DNS |
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| 9/23/2023 | Macon Speedway - Macon, IL Brandt Season Championship "Racing for the Cup" DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks, Hornets, Pro Late Model, Hybrid 600cc Micros | Results | | Jacob Tipton (Hybrid 600cc Micros) | 6th | - | - | DNS |
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