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| 1/1/2020 | Tulsa Expo Raceway - Tulsa, OK Morning Practice / Evening Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Hunter Pruitt (Restricted 'A' Class) | 4th | - | - | - | | Hunter Pruitt (Winged A-Class) | - | - | - | - | | Hunter Pruitt (Stock Non-Wing) | - | - | - | - |
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| 1/2/2020 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Hunter Pruitt (Restricted 'A' Class) | - | 10th | - | - | | Hunter Pruitt (Winged A-Class) | 5th | - | - | - | | Hunter Pruitt (Stock Non-Wing) | 6th | - | - | - |
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| 1/3/2020 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Hunter Pruitt (Restricted 'A' Class) | - | - | - | - | | Hunter Pruitt (Winged A-Class) | - | - | - | - | | Hunter Pruitt (Stock Non-Wing) | - | - | - | - |
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| 1/4/2020 | Tulsa Expo Raceway - Tulsa, OK #WintheDriller Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Hunter Pruitt (Restricted 'A' Class) | 11th | - | 2nd | - | | Hunter Pruitt (Winged A-Class) | - | - | - | - | | Hunter Pruitt (Stock Non-Wing) | - | - | - | - |
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| 5/23/2020 | Southern Illinois Raceway - Marion, IL Points Race/Bailey Chasis Restrictor Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Hunter Pruitt (Winged Outlaw) | 4th | - | - | 17th |
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| 5/30/2020 | Southern Illinois Raceway - Marion, IL Points Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Hunter Pruitt (Winged Outlaw) | 5th | - | - | 11th |
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| 6/6/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Gibson Memorial - Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Hunter Pruitt (Winged Outlaw) | 7th | - | - | 20th (DNF) |
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| 6/20/2020 | Southern Illinois Raceway - Marion, IL Performance Electronics Prelude to the Hustle Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Hunter Pruitt (Winged Outlaw) | 4th | - | - | 20th |
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| 7/3/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship $20K to Win! Winged Outlaw Only Winged Outlaw | Results | | Hunter Pruitt (Winged Outlaw) | 4th | - | 13th | - |
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| 7/4/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship $20K to Win! Winged Outlaw Only Winged Outlaw | Results | | Hunter Pruitt (Winged Outlaw) | 9th (DNF) | - | - | - |
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| 8/21/2020 | Coles County Speedway - Mattoon, IL HART Series Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Hunter Pruitt (Winged Outlaw) | 5th (DNF) | - | - | DNS | | Hunter Pruitt (Winged A-Class) | 1st | - | - | 4th (DNF) |
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| 8/28/2020 | Tri City Speedway - Granite City, IL MOWA 410 Winged Sprints/POWRi WAR Non-Wing Sprints/305 Winged Sprints/Winged Micros 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Non-Winged Sprints: POWRi WAR Sprints 305 Sprints - Winged, Winged Outlaw | Results | | Hunter Pruitt (Winged Outlaw) | 4th | - | - | 7th |
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