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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 | | Hunter Pruitt (Winged Outlaw) | 8th | - | 12th | - |
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| 5/17/2019 | Belle-Clair Speedway - Belleville, IL Southern Illinois Shootout DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged Outlaw, B Modifieds | Results | | Hunter Pruitt (Winged Outlaw) | 8th | - | 15th | - |
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| 5/25/2019 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Hunter Pruitt (Winged Outlaw) | 2nd | - | - | - |
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| 5/31/2019 | Belle-Clair Speedway - Belleville, IL Lucas OIl MLRA Late Models Dirt Super Late Models: Lucas Oil MLRA DIRTcar Late Models, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged Outlaw, B Modifieds | Results | | Hunter Pruitt (Winged Outlaw) | 7th | - | 4th | 17th |
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| 6/28/2019 | Belle-Clair Speedway - Belleville, IL DIRTcar UMP Modifieds, DIRTcar Sportsmans, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged A-Class, B Modifieds | Results | | Hunter Pruitt (Winged A-Class) | DNS | - | 10th | - |
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| 7/6/2019 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Hunter Pruitt (Winged Outlaw) | 4th | - | - | - |
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| 7/11/2019 | Wayne County Speedway - Wayne City, IL Wayne County Fair Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Lightning Sprints | Results | | Hunter Pruitt (Winged Outlaw) | 1st | - | - | 8th (DNF) |
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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 | | Hunter Pruitt (Winged A-Class) | 7th (DNF) | - | - | 9th |
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| 7/19/2019 | Wayne County Speedway - Wayne City, IL Showdown in Bean Town Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Hunter Pruitt (Winged Outlaw) | 3rd | - | - | 15th |
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| 7/20/2019 | Wayne County Speedway - Wayne City, IL Showdown in Bean Town Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Hunter Pruitt (Winged Outlaw) | 6th | - | 4th | - |
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| 7/26/2019 | Belle-Clair Speedway - Belleville, IL Border WARS Midgets: POWRi National Midgets with POWRi Non-Winged Sprints: POWRi WAR Sprints Winged A-Class, B Modifieds | Results | | Hunter Pruitt (Winged A-Class) | 7th | - | 9th | - |
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| 9/20/2019 | Tri City Speedway - Granite City, IL Season Championship - UMP Late Models/UMP Modifieds/B-Modifieds/UMP Crate LM/UMP St. Stocks/Micros DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Hunter Pruitt (Winged Outlaw) | 2nd | - | - | 10th |
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| 9/21/2019 | Southern Illinois Raceway - Marion, IL Race/Chase night 3 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Hunter Pruitt (Sportsman Micros) | 7th (DNF) | - | - | 15th (DNF) |
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| 10/4/2019 | Wayne County Speedway - Wayne City, IL Fall Non-Wing Brawl Featuring HART Non-Wing Micros Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Hunter Pruitt (Restricted 'A' Class) | 1st | - | - | 2nd |
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| 10/5/2019 | Wayne County Speedway - Wayne City, IL Fall Non-Wing Brawl w/ HART Non-Wing Micros Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Hunter Pruitt (Restricted 'A' Class) | 1st | - | - | 2nd |
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| 10/12/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO ShowMe Showdown in Honor of Dean Hathman Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Hunter Pruitt (Restricted 'A' Class) | 1st | - | - | 17th (DNF) |
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| 10/17/2019 | Wayne County Speedway - Wayne City, IL Midgets: USAC National Midgets Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Hunter Pruitt (Restricted 'A' Class) | - | - | - | 3rd |
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| 10/18/2019 | Tri City Speedway - Granite City, IL "Willies Tire B-Mod Bash" Night #1 - B-Modifieds $3,000, A-Modifieds $1,000, Winged Micros $500 DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds | Results | | Hunter Pruitt (Winged Outlaw) | 1st | - | - | 1st |
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| 10/19/2019 | Tri City Speedway - Granite City, IL "Willies Tire B-Mod Bash" Night #2 - B-Mods $3,000, A-Mods $1,000, Non-Wing Micros $500, 4-cylinders DIRTcar UMP Modifieds, DIRTcar Sport Compact, Non-Wing Outlaw, B Modifieds | Results | | Hunter Pruitt (Non-Wing Outlaw) | 1st | - | - | 2nd |
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