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| 1/2/2019 | Tulsa Expo Raceway - Tulsa, OK Practice/Heat Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Nathan Benson (Winged Outlaw) | - | - | - | - | | Nathan Benson (Winged A-Class) | - | - | - | - |
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| 1/3/2019 | Tulsa Expo Raceway - Tulsa, OK Race Day Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Nathan Benson (Winged Outlaw) | 2nd | - | - | - | | Nathan Benson (Winged A-Class) | 2nd | - | - | - |
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| 1/4/2019 | Tulsa Expo Raceway - Tulsa, OK Race Day Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Nathan Benson (Winged Outlaw) | - | 4th | - | - | | Nathan Benson (Winged A-Class) | - | 7th | - | - |
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| 1/5/2019 | Tulsa Expo Raceway - Tulsa, OK Shootout Finale - Golden Driller Day! Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Nathan Benson (Winged Outlaw) | - | 5th | 2nd | 19th | | Nathan Benson (Winged A-Class) | - | - | 5th | - |
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| 5/18/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Winged Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Nathan Benson (Winged Outlaw) | 8th | - | - | - |
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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 | | Nathan Benson (Winged Outlaw) | 1st | - | - | 19th (DNF) |
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| 6/1/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Jr. Sprints Night to Shine - Points Race for ALL Classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Nathan Benson (Winged Outlaw) | 3rd | - | - | 13th (DNF) |
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| 6/8/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Chase and Rodney Gibson Memorial - Points race for ALL classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 16th (DNF) |
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| 6/13/2019 | Brownstown Bullring - Brownstown, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 4th | - | - | 20th |
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| 6/14/2019 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 3rd | - | - | - |
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| 6/21/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Nathan Benson (Winged A-Class) | - | - | - | - |
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| 7/5/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 2nd | - | 4th | 23rd (DNF) |
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| 7/6/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 20th |
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