| | Heat | Dash | B Feature | A Feature |
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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 | | Troy Leonard (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 | | Troy Leonard (Winged A-Class) | 8th | - | - | - |
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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 | | Troy Leonard (Winged A-Class) | - | - | - | - |
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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 | | Troy Leonard (Winged A-Class) | - | - | - | - |
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| 5/31/2020 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Troy Leonard (Winged Outlaw) | 4th | - | - | 9th (DNF) |
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| 6/27/2020 | Southern Illinois Raceway - Marion, IL Points Race/Hart Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Troy Leonard (Sportsman Micros) | 6th | - | - | 6th |
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| 7/10/2020 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Troy Leonard (Winged A-Class) | 2nd | - | - | 1st |
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| 7/26/2020 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Rain Delay Winged A-Class | Results | | Troy Leonard (Winged A-Class) | 7th | - | - | - |
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| 8/8/2020 | Southern Illinois Raceway - Marion, IL Performance Electronics Prelude to the Sprague Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Troy Leonard (Sportsman Micros) | 7th (DNF) | - | - | 9th |
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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 | | Troy Leonard (Winged A-Class) | DNS | - | - | 1st |
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| 8/22/2020 | Southern Illinois Raceway - Marion, IL Points Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Troy Leonard (Sportsman Micros) | 6th | - | - | 8th |
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