| | Heat | Dash | B Feature | A Feature |
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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 | | Rob Cook (Winged Outlaw) | 4th | - | 1st | 10th |
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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 | | Rob Cook (Winged Outlaw) | 3rd | - | 2nd | 22nd |
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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 | | Rob Cook (Winged Outlaw) | 4th | - | 13th | - |
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| 5/31/2019 | Belle-Clair Speedway - Belleville, IL Lucas OIl MLRA Late Models Dirt Super Late Models: Lucas Oil MLRA DIRTcar Late Models, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged Outlaw, B Modifieds | Results | | Rob Cook (Winged Outlaw) | 4th | - | - | 14th |
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| 6/1/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Rob Cook (Winged Outlaw) | DNS | - | DNS | - |
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| 6/13/2019 | Brownstown Bullring - Brownstown, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Rob Cook (Winged Outlaw) | 4th | - | - | 15th |
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| 6/14/2019 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Rob Cook (Winged Outlaw) | 5th | - | - | - |
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| 6/28/2019 | Belle-Clair Speedway - Belleville, IL DIRTcar UMP Modifieds, DIRTcar Sportsmans, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged A-Class, B Modifieds | Results | | Rob Cook (Winged A-Class) | 6th | - | 11th | - |
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| 8/2/2019 | Belle-Clair Speedway - Belleville, IL The Talker Guy 100 DIRTcar Late Models, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged A-Class, B Modifieds | Results | | Rob Cook (Winged A-Class) | 6th | - | - | 9th |
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| 8/3/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Rob Cook (Winged Outlaw) | 6th | - | - | 8th |
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| 8/10/2019 | Southern Illinois Raceway - Marion, IL Race/Dwarf special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Rob Cook (Winged Outlaw) | 8th | - | - | 11th |
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| 8/17/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Rob Cook (Winged Outlaw) | 5th | - | - | DNS |
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| 9/13/2019 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi Winged Outlaw | Results | | Rob Cook (Winged Outlaw) | 4th | - | - | 22nd |
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