| | Heat | Dash | B Feature | A Feature |
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| 4/30/2021 | Coles County Speedway - Mattoon, IL Opening Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jacob Tipton (Winged Outlaw) | 2nd | - | - | 5th |
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| 5/1/2021 | Macon Speedway - Macon, IL CEFCU Kid's Club Regular Night of Racing DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Jacob Tipton (Winged A-Class) | 3rd | - | - | 2nd |
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| 5/15/2021 | Macon Speedway - Macon, IL 95Q Armed Forces Night (Featuring Free Admission for Active and Retired Military DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Jacob Tipton (Winged A-Class) | 2nd | - | - | 2nd |
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| 5/31/2021 | Macon Speedway - Macon, IL Memorial Day Twin 50s - SLM 50 laps & Modifieds 50 laps DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets | Results | | Jacob Tipton (Winged A-Class) | 5th | - | - | 7th |
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| 6/5/2021 | Highland Speedway - Highland, IL Bi State Late Models DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Jacob Tipton (Winged Outlaw) | 3rd | - | - | DNS |
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| 6/12/2021 | Macon Speedway - Macon, IL Taylorville Night Featuring Power Wheels emo Derby & CEFCU Kids DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Jacob Tipton (Winged A-Class) | 3rd | - | - | 3rd |
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| 6/18/2021 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Jacob Tipton (Winged Outlaw) | 4th | - | - | 7th |
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| 7/3/2021 | Macon Speedway - Macon, IL Dynagraphics/95Q Firecracker 40s Pro Late Model/Topless Modified (Fireworks) DIRTcar UMP Modifieds, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Jacob Tipton (Winged A-Class) | 3rd | - | - | 6th |
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| 7/17/2021 | Macon Speedway - Macon, IL Church Night Featuring Faster Pastor Race DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model, Limited Modified | Results | | Jacob Tipton (Winged A-Class) | 2nd | - | - | 2nd |
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| 8/7/2021 | Macon Speedway - Macon, IL Diane Bennett Memorial DIRTcar UMP Modifieds, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Jacob Tipton (Winged A-Class) | 5th | - | - | 6th |
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| 8/28/2021 | Macon Speedway - Macon, IL Skeff Distributing presents IMRA Midgets / Hornet World Championships Economy Midgets, DIRTcar UMP Modifieds, Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Jacob Tipton (Winged A-Class) | 3rd | - | - | 7th |
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| 9/3/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Jacob Tipton (Winged Outlaw) | 3rd | - | - | 1st |
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| 9/10/2021 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Jacob Tipton (Winged Outlaw) | 3rd | - | - | 19th |
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