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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 | | Landon Crawley (Restricted 'A' Class) | 5th | - | - | - | | Landon Crawley (Winged A-Class) | - | - | - | - |
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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 | | Landon Crawley (Restricted 'A' Class) | - | 8th | - | - | | Landon Crawley (Winged A-Class) | 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 | | Landon Crawley (Restricted 'A' Class) | - | - | 2nd | - | | Landon Crawley (Winged A-Class) | - | - | - | - |
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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 | | Landon Crawley (Restricted 'A' Class) | 8th | - | - | 21st | | Landon Crawley (Winged A-Class) | - | - | - | - |
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| 2/15/2019 | Hunt County Raceway - Greenville, TX Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Results | | Landon Crawley (Restricted 'A' Class) | 2nd | - | - | 6th | | Landon Crawley (Winged A-Class) | 9th | - | 6th | - |
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| 2/16/2019 | Hunt County Raceway - Greenville, TX Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Results | | Landon Crawley (Restricted 'A' Class) | 2nd | - | - | 7th | | Landon Crawley (Winged A-Class) | 3rd | - | - | 12th |
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| 3/16/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged, Winged Outlaw | Results | | Landon Crawley (Winged Outlaw) | - | - | - | 7th |
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| 3/23/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged, Winged Outlaw | Results | | Landon Crawley (Winged Outlaw) | - | - | - | 5th |
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| 3/29/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged: ASCS Sooner Region with ASCS Lone Star Region, ASCS Mid-South Region Winged Outlaw | Results | | Landon Crawley (Winged Outlaw) | - | - | - | 13th |
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| 6/1/2019 | I-30 Speedway - Little Rock, AR | Results | | Landon Crawley (Winged Outlaw) | - | - | - | 7th |
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| 6/8/2019 | Port City Raceway - Tulsa, OK Weekly Show - Hot Summer Night! Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Landon Crawley (Winged A-Class) | 4th | - | - | 12th |
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| 6/29/2019 | I-30 Speedway - Little Rock, AR 305 Sprints - Winged: MSCA-Mid-South Sprint Car Association Winged Outlaw | Results | | Landon Crawley (Winged Outlaw) | - | - | - | 5th |
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| 7/5/2019 | Arkoma Speedway - Arkoma, OK Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Rain Out |
| 7/27/2019 | I-30 Speedway - Little Rock, AR 360 Sprints - Winged: ASCS Mid-South Region Winged Outlaw | Results | | Landon Crawley (Winged Outlaw) | - | - | - | 10th |
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| 8/17/2019 | I-30 Speedway - Little Rock, AR Winged Outlaw: NOW600 Outlaw Micros | Results | | Landon Crawley (Winged Outlaw) | 4th | - | - | 2nd |
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| 9/7/2019 | Riverside International Speedway - West Memphis, AR FALL NATIONALS 305 Sprints - Winged: MSCA-Mid-South Sprint Car Association 360 Sprints - Winged, Stock Cars, Winged A-Class, Dirt Late Models | Results | | Landon Crawley (Winged A-Class) | 2nd | - | - | 2nd |
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| 10/19/2019 | I-30 Speedway - Little Rock, AR Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw | Results | | Landon Crawley (Winged Outlaw) | 3rd | - | - | 9th |
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