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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 | | Caden Englehart (Winged Outlaw) | - | - | - | - | | Caden Englehart (Non-Wing Outlaw) | 6th | - | - | - | | Caden Englehart (Winged A-Class) | - | - | - | - | | Caden Englehart (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 | | Caden Englehart (Winged Outlaw) | 8th | - | - | - | | Caden Englehart (Non-Wing Outlaw) | - | - | - | - | | Caden Englehart (Winged A-Class) | 7th | - | - | - | | Caden Englehart (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 | | Caden Englehart (Winged Outlaw) | - | - | - | - | | Caden Englehart (Non-Wing Outlaw) | - | - | - | - | | Caden Englehart (Winged A-Class) | - | - | - | - | | Caden Englehart (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 | | Caden Englehart (Winged Outlaw) | - | - | 10th | - | | Caden Englehart (Non-Wing Outlaw) | - | - | - | - | | Caden Englehart (Winged A-Class) | - | - | - | - | | Caden Englehart (Stock Non-Wing) | - | - | - | - |
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| 6/7/2019 | Coles County Speedway - Mattoon, IL AMSA 2500 to win Outlaw Wing Night 1 Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Caden Englehart (Winged Outlaw) | 5th | - | - | - |
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| 6/8/2019 | Miami County Raceway - Peru, IN Points Race #4 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Caden Englehart (Winged Outlaw) | 5th | - | - | 9th |
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| 7/3/2019 | Miami County Raceway - Peru, IN Firecracker 40's. $1000 to Win Non-Wing Outlaw and Outlaw Wing Plus Huge Fireworks Show! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Caden Englehart (Winged Outlaw) | 4th | - | - | 10th |
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| 7/5/2019 | US 24 Speedway - Logansport, IN rain out make up Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Senior Micros | Results | | Caden Englehart (Winged Outlaw) | 3rd | - | - | 4th |
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| 7/6/2019 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Caden Englehart (Winged Outlaw) | 1st | - | - | - | | Caden Englehart (Non-Wing Outlaw) | 1st | - | - | - |
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