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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 | | Dean Drake Jr (Non-Wing Outlaw) | 3rd | - | - | - |
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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 | | Dean Drake Jr (Non-Wing Outlaw) | - | - | - | - |
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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 | | Dean Drake Jr (Non-Wing Outlaw) | - | - | - | - |
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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 | | Dean Drake Jr (Non-Wing Outlaw) | - | - | 10th | - |
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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 | | Dean Drake Jr (Sportsman Micros) | DNS | - | - | 4th |
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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 | | Dean Drake Jr (Sportsman Micros) | - | - | - | 9th |
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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 | | Dean Drake Jr (Sportsman Micros) | 3rd | - | - | 12th |
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| 10/18/2019 | Caney Valley Speedway - Caney, KS Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Factory Stocks, USRA B-Mods | Results | | Dean Drake Jr (Winged A-Class) | 1st | - | - | 3rd | | Dean Drake Jr (Stock Non-Wing) | 1st | - | - | 3rd |
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| 10/19/2019 | Caney Valley Speedway - Caney, KS Champ 360 Sprints - Winged: Oil Capital Racing Series Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Factory Stocks, Stock Cars, USRA B-Mods | Results | | Dean Drake Jr (Winged A-Class) | - | - | - | 4th | | Dean Drake Jr (Stock Non-Wing) | - | - | - | 3rd |
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