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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 | | Jordan Howell (Winged Outlaw) | - | - | - | - | | Jordan Howell (Non-Wing Outlaw) | 4th | - | - | - |
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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 | | Jordan Howell (Winged Outlaw) | 3rd | - | - | - | | Jordan Howell (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 | | Jordan Howell (Winged Outlaw) | - | 10th | - | - | | Jordan Howell (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 | | Jordan Howell (Winged Outlaw) | - | - | 5th | - | | Jordan Howell (Non-Wing Outlaw) | - | - | - | - |
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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 | | Jordan Howell (Winged Outlaw) | 2nd | - | - | 20th |
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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 | | Jordan Howell (Winged Outlaw) | 2nd | - | - | 11th |
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| 5/10/2019 | Belle-Clair Speedway - Belleville, IL Midwest Season Opener Midgets: POWRi National Midgets with POWRi Winged Outlaw, B Modifieds | Results | | Jordan Howell (Winged Outlaw) | 7th | - | 6th | - |
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| 5/17/2019 | Belle-Clair Speedway - Belleville, IL Southern Illinois Shootout DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged Outlaw, B Modifieds | Results | | Jordan Howell (Winged Outlaw) | 1st | - | - | 17th |
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| 5/18/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Winged Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Jordan Howell (Winged Outlaw) | 1st | - | - | 11th |
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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 | | Jordan Howell (Winged Outlaw) | 6th | - | - | 15th (DNF) | | Jordan Howell (Winged A-Class) | - | - | - | - |
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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 | | Jordan Howell (Winged Outlaw) | 4th | - | - | 22nd (DNF) |
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| 7/5/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Jordan Howell (Winged Outlaw) | 6th | - | 6th | 13th |
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| 7/6/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Jordan Howell (Winged Outlaw) | 2nd | - | 7th | - |
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| 7/12/2019 | Valley Speedway - Grain Valley, MO Thunder In the Valley National Midgets by Rod End Supply Midgets: POWRi National Midgets with POWRi West Midgets Sprint Cars, Winged Outlaw | Results | | Jordan Howell (Winged Outlaw) | 2nd | - | - | 6th |
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| 7/13/2019 | Valley Speedway - Grain Valley, MO Thunder in the Valley National midgets by Rod End Supply Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw | Results | | Jordan Howell (Winged Outlaw) | 6th | - | - | 13th |
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| 8/23/2019 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Winged A-Class | Results | | Jordan Howell (Winged A-Class) | 3rd | - | 3rd | 12th |
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| 8/24/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Jordan Howell (Winged A-Class) | 5th | - | 13th (DNF) | - |
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| 8/31/2019 | Lake Ozark Speedway - Eldon, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Midgets: POWRi National Midgets with POWRi West Midgets | Results | | Jordan Howell (Midgets) | 7th | - | - | 14th |
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| 9/1/2019 | Lake Ozark Speedway - Eldon, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Midgets: POWRi National Midgets with POWRi West Midgets | Results | | Jordan Howell (Midgets) | 8th | - | - | 21st |
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| 9/6/2019 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets Winged Outlaw | Results | | Jordan Howell (Winged Outlaw) | 3rd | - | - | 10th |
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| 9/13/2019 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi Winged Outlaw | Results | | Jordan Howell (Winged Outlaw) | 6th | - | 5th | 15th |
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| 9/14/2019 | Macon Speedway - Macon, IL Midgets: POWRi Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks | Results | | Jordan Howell (Winged Outlaw) | 6th | - | - | 12th | | Jordan Howell (Winged A-Class) | - | - | - | 12th |
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| 10/12/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Midgets: POWRi National Midgets Winged Outlaw | Results | | Jordan Howell (Winged Outlaw) | 2nd | - | - | 2nd |
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| 10/13/2019 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi Winged Outlaw, B Modifieds | Results | | Jordan Howell (Winged Outlaw) | 3rd | - | - | 7th |
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