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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 | | Nathan Benson (Winged Outlaw) | - | - | - | - | | Nathan Benson (Winged A-Class) | - | - | - | - |
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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 | | Nathan Benson (Winged Outlaw) | 2nd | - | - | - | | Nathan Benson (Winged A-Class) | 3rd | - | - | - |
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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 | | Nathan Benson (Winged Outlaw) | - | - | - | - | | Nathan Benson (Winged A-Class) | - | 7th | - | - |
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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 | | Nathan Benson (Winged Outlaw) | 5th | 4th | 1st | 13th | | Nathan Benson (Winged A-Class) | - | - | 4th | - |
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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 | | Nathan Benson (Winged Outlaw) | 2nd | - | 5th | 11th |
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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 | | Nathan Benson (Winged Outlaw) | 3rd | - | 2nd | - |
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| 7/11/2020 | Southern Illinois Raceway - Marion, IL Points Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 1st |
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| 7/24/2020 | Southern Illinois Raceway - Marion, IL Engler Machine and Tool Highbanks Hustle Prelim Winged A-Class, Stock Non-Wing | Results | | Nathan Benson (Winged A-Class) | 1st | - | 1st | 3rd |
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| 7/25/2020 | Southern Illinois Raceway - Marion, IL Engler Machine and Tool Highbanks Hustle Final Winged A-Class, Stock Non-Wing | Results | | Nathan Benson (Winged A-Class) | - | - | - | - |
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| 7/26/2020 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Rain Delay Winged A-Class | Results | | Nathan Benson (Winged A-Class) | - | 3rd | - | 5th |
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| 12/28/2020 | Tulsa Expo Raceway - Tulsa, OK AM: Early Move-In / PM: Regular Move-In Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Nathan Benson (Winged Outlaw) | - | - | - | - |
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| 12/30/2020 | Tulsa Expo Raceway - Tulsa, OK Racing Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, 600cc Modifieds | Results | | Nathan Benson (Winged Outlaw) | 9th | - | - | - |
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| 12/31/2020 | Tulsa Expo Raceway - Tulsa, OK Racing Winged Outlaw, Non-Wing Outlaw, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Nathan Benson (Winged Outlaw) | - | - | - | - |
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