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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 | | Tobias Midkiff (Winged Outlaw) | 9th | - | 18th | - |
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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 | | Tobias Midkiff (Winged Outlaw) | 6th | - | 3rd | 19th |
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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 | | Tobias Midkiff (Winged A-Class) | 6th | - | 9th | - |
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| 7/6/2019 | Macon Speedway - Macon, IL Dean Garland Classic Street Stocks: Midwest Stock Car Tour DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Hornets, Pro Late Model | Results | | Tobias Midkiff (Winged A-Class) | DNS | - | - | 15th (DNF) |
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| 7/13/2019 | Macon Speedway - Macon, IL Miles Chevrolet & Fireman's Ball and First Responders Night DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tobias Midkiff (Winged A-Class) | 4th | - | - | 16th (DNF) |
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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 | | Tobias Midkiff (Non-Wing Outlaw) | 5th (DNF) | - | - | 9th (DNF) |
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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 | | Tobias Midkiff (Non-Wing Outlaw) | 5th | - | - | 9th |
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| 7/26/2019 | Belle-Clair Speedway - Belleville, IL Border WARS Midgets: POWRi National Midgets with POWRi Non-Winged Sprints: POWRi WAR Sprints Winged A-Class, B Modifieds | Results | | Tobias Midkiff (Winged A-Class) | 5th | - | - | 20th |
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| 8/23/2019 | Belle-Clair Speedway - Belleville, IL Big Ten Series DIRTcar Late Models, DIRTcar UMP Modifieds, Winged A-Class, B Modifieds | Results | | Tobias Midkiff (Winged A-Class) | 6th | - | - | 21st |
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| 8/31/2019 | Wayne County Speedway - Wayne City, IL HART Non-Wing/MMSA Labor Day Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Tobias Midkiff (Winged Outlaw) | 7th | - | - | 15th |
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| 9/6/2019 | Tri City Speedway - Granite City, IL Brad Yotter Memorial - UMP Late Models/UMP Mods/B-Mods/UMP Crate LM/Street Stock/Wing Micros DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Tobias Midkiff (Winged Outlaw) | 4th | - | - | 10th |
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| 9/27/2019 | Wayne County Speedway - Wayne City, IL Bean Day Bash Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Tobias Midkiff (Winged Outlaw) | 8th (DNF) | - | - | 16th (DNF) |
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| 10/4/2019 | Wayne County Speedway - Wayne City, IL Fall Non-Wing Brawl Featuring HART Non-Wing Micros Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Tobias Midkiff (Winged Outlaw) | 5th (DNF) | - | - | 11th (DNF) |
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| 10/13/2019 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi Winged Outlaw, B Modifieds | Results | | Tobias Midkiff (Winged Outlaw) | 4th | - | - | 18th |
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