| | Heat | Dash | B Feature | A Feature |
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| 5/10/2019 | Belle-Clair Speedway - Belleville, IL Midwest Season Opener Midgets: POWRi National Midgets with POWRi Winged Outlaw, B Modifieds | Results | | Cole Tinsley (Winged Outlaw) | 6th | - | 5th | - |
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| 5/25/2019 | Southern Illinois Raceway - Marion, IL Race/Armed Forces Night/Restrictor Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Cole Tinsley (Winged Outlaw) | 2nd | - | - | DNS |
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| 6/1/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Cole Tinsley (Winged Outlaw) | 7th | - | - | 13th |
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| 6/21/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Cole Tinsley (Winged A-Class) | - | - | - | - |
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| 7/6/2019 | Macon Speedway - Macon, IL Dean Garland Classic Street Stocks: Midwest Stock Car Tour DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Hornets, Pro Late Model | Results | | Cole Tinsley (Winged A-Class) | 3rd | - | - | 4th |
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| 7/13/2019 | Macon Speedway - Macon, IL Miles Chevrolet & Fireman's Ball and First Responders Night DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Cole Tinsley (Winged A-Class) | 2nd | - | - | 10th |
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| 7/20/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Non-Wing Outlaw: POWRi 600cc Outlaw Micro Sprints Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Cole Tinsley (Winged Outlaw) | 2nd | - | - | 3rd | | Cole Tinsley (Non-Wing Outlaw) | 7th | - | - | 16th (DNF) |
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| 8/3/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Cole Tinsley (Winged Outlaw) | 1st | - | - | 10th |
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| 8/17/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Cole Tinsley (Winged Outlaw) | 2nd | - | - | 4th |
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| 8/23/2019 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Winged A-Class | Results | | Cole Tinsley (Winged A-Class) | 5th | - | 6th | - |
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| 8/24/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Cole Tinsley (Winged A-Class) | 5th | - | 12th (DNF) | - |
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| 9/14/2019 | Macon Speedway - Macon, IL Midgets: POWRi Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks | Results | | Cole Tinsley (Winged Outlaw) | 3rd | - | - | 22nd | | Cole Tinsley (Winged A-Class) | - | - | - | 22nd |
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