| | 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 | | Bret Gale (Winged Outlaw) | 6th | - | 11th | - |
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| 5/11/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Rain Out |
| 5/14/2019 | Wayne County Speedway - Wayne City, IL To Tired to Wait Tuesday Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Bret Gale (Winged Outlaw) | 7th | - | - | 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 | | Bret Gale (Winged Outlaw) | 6th | - | 16th | - |
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| 5/25/2019 | Wayne County Speedway - Wayne City, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Lightning Sprints | Results | | Bret Gale (Winged Outlaw) | DNS | - | - | - | | Bret Gale (Non-Wing Outlaw) | 7th (DNF) | - | - | DNS |
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| 7/19/2019 | Wayne County Speedway - Wayne City, IL Showdown in Bean Town Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Bret Gale (Winged Outlaw) | 7th | - | 8th | - |
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| 7/20/2019 | Wayne County Speedway - Wayne City, IL Showdown in Bean Town Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Bret Gale (Winged Outlaw) | 7th (DNF) | - | DNS | - |
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