| | Heat | Dash | B Feature | A Feature |
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| 9/1/2023 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged, 305 Sprints - Winged, Winged Outlaw, Street Stocks, 604 Crate Late Models | Results | | Coleman Gilpin (Winged Outlaw) | 4th | - | - | 10th |
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| 10/6/2023 | Jacksonville Speedway - Jacksonville, IL Ron Milton Race of Champions 410 Sprints - Winged: MOWA-Midwest Open Wheel Association 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Coleman Gilpin (Winged Outlaw) | 4th | - | - | 5th |
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| 10/7/2023 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros, HART Non-Wing Micros | Results | | Coleman Gilpin (Winged Outlaw) | 6th | - | - | 9th |
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| 11/4/2023 | Wayne County Speedway - Wayne City, IL Fall Spectacular Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Coleman Gilpin (Winged Outlaw) | 3rd | - | - | 5th |
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| 12/26/2023 | Tulsa Expo Raceway - Tulsa, OK Shootout Parking / Check-In Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Coleman Gilpin (Winged Outlaw) | - | - | - | - | | Coleman Gilpin (Non-Wing Outlaw) | - | - | - | - | | Coleman Gilpin (Stock Non-Wing) | - | - | - | - |
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| 12/27/2023 | Tulsa Expo Raceway - Tulsa, OK Morning Practice Then Racing Winged Outlaw: Tulsa Shootout | Results | | Coleman Gilpin (Winged Outlaw) | 9th | - | - | - |
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| 12/28/2023 | Tulsa Expo Raceway - Tulsa, OK Racing - Day 2 Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Coleman Gilpin (Winged Outlaw) | - | - | - | - | | Coleman Gilpin (Non-Wing Outlaw) | 8th | - | - | - |
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| 12/29/2023 | Tulsa Expo Raceway - Tulsa, OK Racing - Day 3 Non-Wing Outlaw, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Coleman Gilpin (Non-Wing Outlaw) | - | - | - | - |
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