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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 | | Adrian Cobbs (Winged Outlaw) | - | - | - | - | | Adrian Cobbs (Non-Wing Outlaw) | - | - | - | - | | Adrian Cobbs (Winged A-Class) | - | - | - | - | | Adrian Cobbs (Stock Non-Wing) | - | - | - | - |
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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 | | Adrian Cobbs (Winged Outlaw) | - | - | - | - | | Adrian Cobbs (Winged A-Class) | 7th | - | - | - | | Adrian Cobbs (Stock Non-Wing) | 6th | - | - | - |
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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 | | Adrian Cobbs (Winged Outlaw) | - | - | - | - | | Adrian Cobbs (Winged A-Class) | - | - | - | - | | Adrian Cobbs (Stock Non-Wing) | - | - | - | - |
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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 | | Adrian Cobbs (Winged Outlaw) | - | - | - | - | | Adrian Cobbs (Winged A-Class) | - | - | 11th | - | | Adrian Cobbs (Stock Non-Wing) | - | - | - | - |
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| 3/29/2019 | Port City Raceway - Tulsa, OK 8th Annual Donnie Ray Crawford Memorial Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Adrian Cobbs (Winged A-Class) | 6th | - | 7th | - | | Adrian Cobbs (Stock Non-Wing) | 6th | - | DNS | - |
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| 3/30/2019 | Port City Raceway - Tulsa, OK 8th Annual Donnie Ray Crawford Memorial Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Adrian Cobbs (Winged A-Class) | 2nd | - | - | 20th | | Adrian Cobbs (Stock Non-Wing) | 3rd | - | DNS | - |
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| 4/6/2019 | Port City Raceway - Tulsa, OK Weekly Show Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds, Sportsman Micros, Senior Micros | Results | | Adrian Cobbs (Winged A-Class) | 1st | - | - | 4th | | Adrian Cobbs (Stock Non-Wing) | 1st | - | - | 11th |
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| 4/20/2019 | Port City Raceway - Tulsa, OK Weekly Show Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Adrian Cobbs (Winged A-Class) | 4th | - | - | 10th |
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| 6/1/2019 | Port City Raceway - Tulsa, OK Weekly Show - Tulsa County Night Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Adrian Cobbs (Winged Outlaw) | 6th | - | DNS | - | | Adrian Cobbs (Winged A-Class) | 6th | - | 10th | - |
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