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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 | | Darien Roberts (Non-Wing Outlaw) | 4th | - | - | - | | Darien Roberts (Winged A-Class) | - | - | - | - | | Darien Roberts (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 | | Darien Roberts (Non-Wing Outlaw) | - | - | - | - | | Darien Roberts (Winged A-Class) | 2nd | - | - | - | | Darien Roberts (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 | | Darien Roberts (Non-Wing Outlaw) | - | - | - | - | | Darien Roberts (Winged A-Class) | - | 8th | - | - | | Darien Roberts (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 | | Darien Roberts (Non-Wing Outlaw) | - | - | - | - | | Darien Roberts (Winged A-Class) | - | - | 4th | - | | Darien Roberts (Stock Non-Wing) | - | - | - | - |
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| 3/16/2019 | Port City Raceway - Tulsa, OK Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Junior Sprints, 600cc Modifieds, Sportsman Micros | Results | | Darien Roberts (Winged A-Class) | 1st | - | - | 17th | | Darien Roberts (Stock Non-Wing) | 1st | - | - | 16th |
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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 | | Darien Roberts (Winged Outlaw) | 3rd | - | - | 7th | | Darien Roberts (Winged A-Class) | 2nd | - | - | 3rd | | Darien Roberts (Stock Non-Wing) | 2nd | - | - | 17th |
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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 | | Darien Roberts (Winged Outlaw) | 4th | - | - | 20th | | Darien Roberts (Winged A-Class) | - | - | - | 4th | | Darien Roberts (Stock Non-Wing) | 5th | - | 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 | | Darien Roberts (Winged Outlaw) | 3rd | - | - | 1st | | Darien Roberts (Winged A-Class) | 4th | - | - | 18th | | Darien Roberts (Stock Non-Wing) | DNS | - | 2nd | 7th |
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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 | | Darien Roberts (Stock Non-Wing) | 2nd | - | - | 17th |
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