| | Heat | Dash | B Feature | A Feature |
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| 3/24/2019 | Port City Raceway - Tulsa, OK Turnpike Challenge - POWRi Lucas Oil National Midgets and POWRi Outlaw Micros Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw | Results | | Charlie Crawford (Winged Outlaw) | 2nd | - | - | 22nd |
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| 4/27/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Non-Points Race for all Classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Charlie Crawford (Stock Non-Wing) | 3rd | - | - | 5th |
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| 6/1/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Jr. Sprints Night to Shine - Points Race for ALL Classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Charlie Crawford (Stock Non-Wing) | 7th | - | - | 23rd (DNF) |
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| 6/8/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Chase and Rodney Gibson Memorial - Points race for ALL classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Charlie Crawford (Stock Non-Wing) | 2nd | - | - | 8th |
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| 6/21/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Charlie Crawford (Winged A-Class) | - | - | - | - |
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| 7/5/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Charlie Crawford (Winged Outlaw) | 6th | - | 8th | 18th |
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| 7/6/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Charlie Crawford (Winged Outlaw) | 10th | - | 13th | - |
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| 7/26/2019 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Stock Non-Wing | Results | | Charlie Crawford (Stock Non-Wing) | 3rd | - | 12th | - |
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| 7/27/2019 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Stock Non-Wing | Results | | Charlie Crawford (Stock Non-Wing) | 6th | - | 6th | - |
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| 8/3/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Points Race for ALL Classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Charlie Crawford (Stock Non-Wing) | 1st | - | - | 13th |
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| 9/14/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Points Race for ALL Classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Charlie Crawford (Stock Non-Wing) | 5th | - | - | 22nd (DNF) |
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| 10/12/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO ShowMe Showdown in Honor of Dean Hathman Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Charlie Crawford (Non-Wing Outlaw) | 3rd | - | - | DNS |
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