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| 3/3/2023 | Wayne County Speedway - Wayne City, IL Midwest Winter Nationals Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Tobias Midkiff (Winged Outlaw) | 7th | - | - | DNS |
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| 3/4/2023 | Wayne County Speedway - Wayne City, IL Midwest Winter Nationals Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Tobias Midkiff (Winged Outlaw) | 7th | - | - | 13th |
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| 3/10/2023 | Wayne County Speedway - Wayne City, IL Season Opener Non-Wing Outlaw, Junior Sprints | Results | | Tobias Midkiff (Non-Wing Outlaw) | 6th | - | - | 13th |
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| 3/11/2023 | Wayne County Speedway - Wayne City, IL Xtreme Outlaw Series National Midgets Non-Wing Outlaw, Junior Sprints | Results | | Tobias Midkiff (Non-Wing Outlaw) | 4th | - | - | 11th |
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| 4/1/2023 | Doe Run Raceway - Doe Run, MO 3rd Annual Small Tire Shootout Winged Outlaw, Restricted 'A' Class, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Tobias Midkiff (Winged Outlaw) | 4th | - | DNS | - |
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| 4/14/2023 | Doe Run Raceway - Doe Run, MO Regular Night of Races Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Tobias Midkiff (Winged Outlaw) | 3rd | - | - | 8th |
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| 4/15/2023 | Macon Speedway - Macon, IL POWRi Micros at Macon Speedway DIRTcar Sportsmans, Winged Outlaw, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tobias Midkiff (Winged Outlaw) | 5th | - | - | 6th |
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| 4/21/2023 | Jacksonville Speedway - Jacksonville, IL Opening Night 410 Sprints - Winged, 305 Sprints - Winged, DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Tobias Midkiff (Winged Outlaw) | 2nd | - | - | 7th |
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| 4/22/2023 | Highland Speedway - Highland, IL Points Night DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Young Guns | Results | | Tobias Midkiff (Winged Outlaw) | 6th | - | 2nd | 19th |
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| 5/5/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Midgets: POWRi National Midgets with POWRi West Midgets Non-Winged Sprints: POWRi WAR Sprints Winged Outlaw | Results | | Tobias Midkiff (Winged Outlaw) | 8th | - | - | 14th |
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| 5/12/2023 | Jacksonville Speedway - Jacksonville, IL $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions 305 Sprints - Winged, Winged Outlaw | Results | | Tobias Midkiff (Winged Outlaw) | 5th | - | - | 11th |
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| 5/19/2023 | Doe Run Raceway - Doe Run, MO Regular Night of Races all classes" rained out before features" Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Tobias Midkiff (Winged Outlaw) | 5th | - | - | DNS |
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| 5/20/2023 | Highland Speedway - Highland, IL Points Night DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Young Guns, Sport Compact | Results | | Tobias Midkiff (Winged Outlaw) | 4th | - | - | 14th |
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| 5/26/2023 | Macon Speedway - Macon, IL Cornfield Combat Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, HART Non-Wing Micros | Results | | Tobias Midkiff (HART Non-Wing Micros) | 8th | - | - | - |
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| 5/27/2023 | Macon Speedway - Macon, IL Cornfield Combat with $5,000 to win Non Wing Micros Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, HART Non-Wing Micros | Results | | Tobias Midkiff (HART Non-Wing Micros) | 7th | - | 11th (DNF) | - |
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| 6/23/2023 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets 410 Sprints - Winged, Winged Outlaw, Street Stocks | Results | | Tobias Midkiff (Winged Outlaw) | 5th | - | - | 11th |
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| 6/24/2023 | Macon Speedway - Macon, IL Illinois SPEED Week Midgets: POWRi National Midgets DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Tobias Midkiff (Winged Outlaw) | 8th | - | - | 14th |
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| 7/15/2023 | Macon Speedway - Macon, IL POWRi Micros at Macon Speedway DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Tobias Midkiff (Winged Outlaw) | 6th (DNF) | - | - | 12th |
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| 7/21/2023 | Doe Run Raceway - Doe Run, MO POWRi Midgets at Doe Run Raceway Midgets: POWRi National Midgets with Xtreme Outlaw Midgets Non-Wing Outlaw, Stock Non-Wing, Mod Lites, Hybrid 600cc Micros | Results | | Tobias Midkiff (Stock Non-Wing) | 5th | - | 5th | - |
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| 7/22/2023 | Highland Speedway - Highland, IL Points Night DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Young Guns | Results | | Tobias Midkiff (Winged Outlaw) | 6th | - | - | 13th |
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| 8/11/2023 | Doe Run Raceway - Doe Run, MO Fan Appreciation night $7 grandstands plus meet the drivers. Regular Night of Races all classes Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Tobias Midkiff (Winged Outlaw) | DNS | - | - | DNS |
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| 8/18/2023 | Doe Run Raceway - Doe Run, MO 30 lap spectator race $300 to win plus all regular classes. Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Tobias Midkiff (Winged Outlaw) | 4th | - | - | 19th |
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| 8/25/2023 | Doe Run Raceway - Doe Run, MO 30 lap pro4/Mini Stock $350 to win Plus all regular classes Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Tobias Midkiff (Winged Outlaw) | 6th | - | - | 15th |
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| 10/11/2023 | Creek County Speedway - Sapulpa, OK Sooner State Showdown Midgets: POWRi National Midgets with POWRi West Midgets Champ 360 Sprints - Winged, Winged Outlaw, Winged A-Class | Results | | Tobias Midkiff (Winged Outlaw) | 4th | - | - | 4th |
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| 10/12/2023 | Port City Raceway - Tulsa, OK 4th Annual DRC Sooner State 55 Midgets: POWRi National Midgets with POWRi West Midgets, Xtreme Outlaw Midgets Winged Outlaw | Results | | Tobias Midkiff (Winged Outlaw) | 8th | - | - | 14th |
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| 10/13/2023 | I-44 Riverside Speedway - Oklahoma City, OK Xtreme Outlaw Midgets Midgets: POWRi National Midgets with POWRi West Midgets, Xtreme Outlaw Midgets Winged Outlaw, Junior Sprints | Results | | Tobias Midkiff (Winged Outlaw) | 8th | - | - | 24th |
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| 10/14/2023 | I-44 Riverside Speedway - Oklahoma City, OK Xtreme Outlaw Midgets Midgets: POWRi National Midgets with POWRi West Midgets, Xtreme Outlaw Midgets Winged Outlaw, Junior Sprints | Results | | Tobias Midkiff (Winged Outlaw) | 7th | - | - | 18th |
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| 10/21/2023 | Riverside International Speedway - West Memphis, AR Mid South Micro Nationals 305 Sprints - Winged, Stock Cars, A Modifieds, Winged A-Class | Results | | Tobias Midkiff (Winged A-Class) | 9th | - | 3rd | 15th |
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