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| 3/21/2019 | Creek County Speedway - Sapulpa, OK 6th Annual Turnpike Challenge Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw | Results | | Matt Carr (Winged Outlaw) | 8th | - | 5th | 14th |
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| 3/22/2019 | I-44 Riverside Speedway - Oklahoma City, OK POWRi Lucas Oil National & West Midget League, POWRi Outlaws & A-Class Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw, Winged A-Class | Results | | Matt Carr (Winged Outlaw) | 3rd | - | - | 9th |
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| 3/23/2019 | I-44 Riverside Speedway - Oklahoma City, OK POWRi Lucas Oil National & West Midget League, POWRi Outlaws & Non-Wing Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw, Stock Non-Wing | Results | | Matt Carr (Winged Outlaw) | 4th | - | - | 23rd |
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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 | | Matt Carr (Winged Outlaw) | 1st | - | - | 9th |
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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 | | Matt Carr (Winged Outlaw) | 2nd | - | 2nd | 19th |
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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 | | Matt Carr (Winged Outlaw) | 2nd | - | 4th | 20th |
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| 6/13/2019 | Brownstown Bullring - Brownstown, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Matt Carr (Winged Outlaw) | 3rd | - | - | 11th |
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| 6/14/2019 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Matt Carr (Winged Outlaw) | 5th | - | - | - |
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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 | | Matt Carr (Winged Outlaw) | 6th | - | - | 10th |
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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 | | Matt Carr (Winged Outlaw) | 2nd | - | - | 10th |
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