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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 | | Cade Cowles (Non-Wing Outlaw) | 1st | - | - | - | | Cade Cowles (Winged A-Class) | - | - | - | - | | Cade Cowles (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 | | Cade Cowles (Non-Wing Outlaw) | - | - | - | - | | Cade Cowles (Winged A-Class) | 8th | - | - | - | | Cade Cowles (Stock Non-Wing) | 7th | - | - | - |
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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 | | Cade Cowles (Non-Wing Outlaw) | - | 5th | - | - | | Cade Cowles (Winged A-Class) | - | - | - | - | | Cade Cowles (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 | | Cade Cowles (Non-Wing Outlaw) | - | - | 9th | - | | Cade Cowles (Winged A-Class) | - | - | - | - | | Cade Cowles (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 | | Cade Cowles (Stock Non-Wing) | 3rd | - | - | 12th |
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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 | | Cade Cowles (Stock Non-Wing) | 1st | - | - | 18th |
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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 | | Cade Cowles (Stock Non-Wing) | 4th | - | - | 18th |
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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 | | Cade Cowles (Stock Non-Wing) | 3rd | - | - | 15th |
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| 4/27/2019 | Port City Raceway - Tulsa, OK Weekly Show - POWRi West Midgets - Autism Night Midgets: POWRi West Midgets Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Cade Cowles (Stock Non-Wing) | 7th | - | 9th | - |
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| 5/4/2019 | Port City Raceway - Tulsa, OK Weekly Show - Cinco De Mayo Night Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Cade Cowles (Stock Non-Wing) | 2nd | - | - | 17th |
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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 | | Cade Cowles (Stock Non-Wing) | 7th | - | 13th | - |
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| 6/15/2019 | Port City Raceway - Tulsa, OK Sooner 600 Week - Night 4 Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Winged Outlaw, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Cade Cowles (Stock Non-Wing) | 6th | - | 5th | - |
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| 6/16/2019 | Arkoma Speedway - Arkoma, OK Sooner 600 Week - Finale Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Results | | Cade Cowles (Stock Non-Wing) | 4th | - | - | 7th |
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| 6/28/2019 | Port City Raceway - Tulsa, OK Non-Wing Nationals Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Cade Cowles (Winged A-Class) | 1st | - | - | 16th |
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| 6/29/2019 | Port City Raceway - Tulsa, OK Non-Wing Nationals Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Cade Cowles (Winged A-Class) | 3rd | - | 17th | - |
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