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| 5/16/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Tobias Midkiff (Winged Outlaw) | 8th | - | - | 17th (DNF) |
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| 6/26/2020 | Wayne County Speedway - Wayne City, IL PureMax HART Series presented by EMi at Doe Run Non-Wing Outlaw | Results | | Tobias Midkiff (Non-Wing Outlaw) | 8th | - | - | DNS |
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| 6/27/2020 | Southern Illinois Raceway - Marion, IL Points Race/Hart Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Tobias Midkiff (Non-Wing Outlaw) | 10th (DNF) | - | 2nd | 22nd (DNF) |
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| 7/11/2020 | Southern Illinois Raceway - Marion, IL Points Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Tobias Midkiff (Winged Outlaw) | 8th (DNF) | - | - | DNS |
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| 8/7/2020 | Coles County Speedway - Mattoon, IL HART Series Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Tobias Midkiff (Non-Wing Outlaw) | 5th | - | - | 19th (DNF) |
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| 8/21/2020 | Coles County Speedway - Mattoon, IL HART Series Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Tobias Midkiff (Non-Wing Outlaw) | - | - | - | 18th (DNF) |
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| 8/21/2020 | Wayne County Speedway - Wayne City, IL HART at Coles County Speedway Non-Wing Outlaw | Results | | Tobias Midkiff (Non-Wing Outlaw) | 6th | - | 2nd | 18th (DNF) |
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| 8/28/2020 | Tri City Speedway - Granite City, IL MOWA 410 Winged Sprints/POWRi WAR Non-Wing Sprints/305 Winged Sprints/Winged Micros 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Non-Winged Sprints: POWRi WAR Sprints 305 Sprints - Winged, Winged Outlaw | Results | | Tobias Midkiff (Winged Outlaw) | 4th | - | - | 10th |
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| 8/29/2020 | Wayne County Speedway - Wayne City, IL Opening Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Tobias Midkiff (Winged Outlaw) | 7th | - | - | 16th (DNF) |
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| 9/4/2020 | Tri City Speedway - Granite City, IL "Test Drive Technologies Night" LM/Mod/BMod/St.Stock/4-Cyl/Winged Micros plus Kids Power Wheels DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Winged Outlaw, B Modifieds, Street Stocks | Results | | Tobias Midkiff (Winged Outlaw) | 2nd | - | - | 2nd |
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| 9/5/2020 | Wayne County Speedway - Wayne City, IL Showdown in Beantown Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints | Results | | Tobias Midkiff (Winged Outlaw) | 6th | - | 9th | - |
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| 9/6/2020 | Wayne County Speedway - Wayne City, IL Showdown in Beantown Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Tobias Midkiff (Winged Outlaw) | 7th | - | 9th | - |
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| 9/12/2020 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Championship Night Stock Non-Wing | Results | | Tobias Midkiff (Stock Non-Wing) | 10th | - | - | - |
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| 9/13/2020 | Macon Speedway - Macon, IL 75th Season of Racing Celebration presented by Decatur Area Convention & Visitors Bureau DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Tobias Midkiff (Winged A-Class) | 9th | - | - | 14th |
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| 9/18/2020 | Tri City Speedway - Granite City, IL "Fan Appreciation/Big Kids Night" 1/2 Price $8 LM/Mod/BMod/St Stocks/4-Cyl/Winged Micros DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Winged Outlaw, B Modifieds, Street Stocks | Results | | Tobias Midkiff (Winged Outlaw) | 7th | - | - | 6th |
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| 9/25/2020 | Wayne County Speedway - Wayne City, IL Trump 45 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Tobias Midkiff (Winged Outlaw) | 5th | - | - | DNS |
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| 10/2/2020 | Tri City Speedway - Granite City, IL POWRI Midgets/MOWA Sprint /305 Sprints/HART Non-Winged Micros 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi 305 Sprints - Winged, Non-Wing Outlaw | Results | | Tobias Midkiff (Non-Wing Outlaw) | 5th | - | - | 17th |
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| 10/9/2020 | Jacksonville Speedway - Jacksonville, IL Ron Milton Race of Champions Midgets: POWRi 410 Sprints - Winged, Winged Outlaw | Results | | Tobias Midkiff (Winged Outlaw) | 4th | - | - | 20th |
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