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| 2/26/2021 | Southern Illinois Center - Duquoin, IL Midwest Winter Nationals Non-Wing Outlaw | Results | | Alex Midkiff (Non-Wing Outlaw) | - | - | - | - |
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| 2/26/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 1 - Night 1 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints | Results | | Alex Midkiff (Winged Outlaw) | 7th | - | 4th | 13th | | Alex Midkiff (Non-Wing Outlaw) | 8th | - | 11th | - |
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| 2/27/2021 | Southern Illinois Center - Duquoin, IL Midwest Winter Nationals Non-Wing Outlaw | Results | | Alex Midkiff (Non-Wing Outlaw) | - | - | - | - |
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| 2/27/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 1 - Night 2 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints | Results | | Alex Midkiff (Winged Outlaw) | 6th | - | 2nd | 12th | | Alex Midkiff (Non-Wing Outlaw) | 2nd | - | 7th | - |
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| 3/5/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 2 - Night 1 Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Alex Midkiff (Non-Wing Outlaw) | 6th | - | - | - |
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| 3/6/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 2 - Night 2 Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Alex Midkiff (Non-Wing Outlaw) | - | - | - | 20th |
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| 3/12/2021 | Southern Illinois Center - Duquoin, IL Midwest Winter Nationals Non-Wing Outlaw | Results | | Alex Midkiff (Non-Wing Outlaw) | - | - | - | 10th |
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| 3/12/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 3 - Night 1 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Alex Midkiff (Winged Outlaw) | 4th | - | - | 9th | | Alex Midkiff (Non-Wing Outlaw) | 2nd | - | - | 10th |
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| 3/13/2021 | Southern Illinois Center - Duquoin, IL Midwest Winter Nationals Non-Wing Outlaw | Results | | Alex Midkiff (Non-Wing Outlaw) | - | - | - | - |
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| 3/13/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 3 - Night 2 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Alex Midkiff (Winged Outlaw) | 8th | - | - | 12th | | Alex Midkiff (Non-Wing Outlaw) | 8th | - | 5th | - |
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| 4/16/2021 | Tri City Speedway - Granite City, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw | Results | | Alex Midkiff (Winged Outlaw) | 3rd | - | - | 6th |
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| 4/17/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Alex Midkiff (Winged Outlaw) | 3rd | - | - | 20th |
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| 4/30/2021 | Tri City Speedway - Granite City, IL Fast Friday Racing UMP LM, UMP Mods, BMods, UMP St Stk, UMP 4-Cyl & Winged Micros DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Winged Outlaw, B Modifieds, Street Stocks | Results | | Alex Midkiff (Winged Outlaw) | 1st | - | - | 4th |
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| 5/1/2021 | Macon Speedway - Macon, IL CEFCU Kid's Club Regular Night of Racing DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Alex Midkiff (Winged A-Class) | 2nd | - | - | 3rd |
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| 5/7/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Alex Midkiff (Winged Outlaw) | 2nd | - | - | 6th |
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| 5/8/2021 | Southern Illinois Raceway - Marion, IL Points Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Alex Midkiff (Winged Outlaw) | 5th | - | - | 6th |
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| 5/15/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Alex Midkiff (Winged Outlaw) | 4th | - | - | 10th |
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| 5/21/2021 | Charleston Speedway - Charleston, IL ILLIANA Showdown Midgets: POWRi National Midgets with POWRi Non-Winged Sprints: POWRi WAR Sprints Winged Outlaw | Results | | Alex Midkiff (Winged Outlaw) | 8th | - | - | 18th |
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| 5/22/2021 | Charleston Speedway - Charleston, IL ILLIANA Showdown Midgets: POWRi National Midgets with POWRi Non-Winged Sprints: POWRi WAR Sprints Winged Outlaw | Results | | Alex Midkiff (Winged Outlaw) | 7th | - | - | 14th |
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| 5/31/2021 | Macon Speedway - Macon, IL Memorial Day Twin 50s - SLM 50 laps & Modifieds 50 laps DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets | Results | | Alex Midkiff (Winged A-Class) | 7th | - | - | 10th |
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| 6/4/2021 | Tri City Speedway - Granite City, IL "4-Cyl Takeover" LM, Mods, BMods, St Stk, Wing Micros $500, 4-cyl $1000,$800,$600 + Kids Power Wheel DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Winged Outlaw, B Modifieds, Street Stocks | Results | | Alex Midkiff (Winged Outlaw) | 5th | - | - | 15th |
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| 6/5/2021 | Southern Illinois Raceway - Marion, IL Performance Electronics Prelude to the Hustle Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Alex Midkiff (Winged Outlaw) | 8th | - | 6th | - | | Alex Midkiff (Non-Wing Outlaw) | 2nd | - | - | 4th |
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| 6/12/2021 | Southern Illinois Raceway - Marion, IL Bailey Chasis Restrictor Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Alex Midkiff (Non-Wing Outlaw) | 5th | - | - | 7th |
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| 6/16/2021 | Charleston Speedway - Charleston, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Alex Midkiff (Winged Outlaw) | 5th | - | - | 14th |
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| 6/17/2021 | Lincoln Speedway - Lincoln, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi DIRTcar UMP Modifieds, Winged Outlaw, Pro Late Model | Results | | Alex Midkiff (Winged Outlaw) | 3rd | - | - | 11th |
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| 6/18/2021 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Alex Midkiff (Winged Outlaw) | 5th | - | - | 9th |
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| 6/19/2021 | Macon Speedway - Macon, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw, Winged A-Class, Street Stocks, Pro Late Model | Results | | Alex Midkiff (Winged Outlaw) | 5th | - | - | 6th | | Alex Midkiff (Winged A-Class) | - | - | - | 6th |
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| 6/20/2021 | Brownstown Bullring - Brownstown, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Alex Midkiff (Winged Outlaw) | 6th | - | - | 6th |
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| 6/26/2021 | Southern Illinois Raceway - Marion, IL Points Night/HART Non-Wing Series Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Alex Midkiff (Winged Outlaw) | 3rd | - | - | 4th | | Alex Midkiff (Non-Wing Outlaw) | 3rd | - | - | 22nd (DNF) |
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| 7/3/2021 | Wayne County Speedway - Wayne City, IL Season Opener Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Alex Midkiff (Winged Outlaw) | 8th | - | - | 8th |
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| 7/9/2021 | Coles County Speedway - Mattoon, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Alex Midkiff (Winged Outlaw) | 2nd | - | - | 2nd | | Alex Midkiff (Non-Wing Outlaw) | 4th | - | - | 9th |
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| 7/17/2021 | Southern Illinois Raceway - Marion, IL Ike Dealership JR Sprint Special/Rising Stars Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Alex Midkiff (Winged Outlaw) | 7th | - | - | 14th (DNF) |
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| 7/22/2021 | Wayne County Speedway - Wayne City, IL Hart Non-Wing Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Alex Midkiff (Winged Outlaw) | 2nd | - | - | 5th |
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| 7/24/2021 | Southern Illinois Raceway - Marion, IL Points Night/HART Non-Wing Series Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Alex Midkiff (Winged Outlaw) | 3rd | - | - | 5th |
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| 8/7/2021 | Wayne County Speedway - Wayne City, IL Hyper NON-Wing Outlaws $1250 to win Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Alex Midkiff (Winged Outlaw) | 6th | - | 2nd | 17th | | Alex Midkiff (Non-Wing Outlaw) | 3rd | - | - | 10th |
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| 8/14/2021 | Macon Speedway - Macon, IL HART Non Wing Micros DIRTcar UMP Modifieds, Non-Wing Outlaw, Stock Non-Wing, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Alex Midkiff (Non-Wing Outlaw) | 4th | - | - | 15th |
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| 8/15/2021 | Jacksonville Speedway - Jacksonville, IL Central Illinois' Non-Wing Swing Night #2 410 Sprints - Winged, Non-Wing Outlaw | Results | | Alex Midkiff (Non-Wing Outlaw) | 3rd | - | - | 5th |
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| 8/20/2021 | Charleston Speedway - Charleston, IL POWRi at Charleston Speedway Midgets: POWRi National Midgets with POWRi Winged Outlaw, Hornets, DIRTcar Pro Modifieds | Results | | Alex Midkiff (Winged Outlaw) | 5th | - | - | 6th |
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| 8/27/2021 | Wayne County Speedway - Wayne City, IL Showdown in Beantown Night #1 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Alex Midkiff (Winged Outlaw) | 7th | - | 12th (DNF) | - |
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| 8/28/2021 | Wayne County Speedway - Wayne City, IL Showdown in Beantown Night #2 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Alex Midkiff (Winged Outlaw) | 7th | - | 6th | - |
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| 9/1/2021 | Wayne County Speedway - Wayne City, IL DuQuoin State Fair Midgets, Non-Wing Outlaw, Restricted 'A' Class | Results | | Alex Midkiff (Non-Wing Outlaw) | 1st | - | - | 2nd |
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| 9/10/2021 | Coles County Speedway - Mattoon, IL Hart Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Alex Midkiff (Non-Wing Outlaw) | 6th | - | - | 12th (DNF) |
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| 9/11/2021 | Wayne County Speedway - Wayne City, IL Remembrance Weekend HART & MMSA Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints | Results | | Alex Midkiff (Non-Wing Outlaw) | 7th | - | 4th | 15th (DNF) |
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| 9/24/2021 | Wayne County Speedway - Wayne City, IL Dan Robinson Memorial Night #1 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Alex Midkiff (Non-Wing Outlaw) | 7th | - | 7th | - |
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| 9/25/2021 | Wayne County Speedway - Wayne City, IL Dan Robinson Memorial Night #2 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Alex Midkiff (Non-Wing Outlaw) | 4th | - | - | 17th |
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| 10/9/2021 | Southern Illinois Raceway - Marion, IL Open Race/Chase Make-up Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Alex Midkiff (Non-Wing Outlaw) | 6th | - | - | 6th |
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| 11/6/2021 | Wayne County Speedway - Wayne City, IL Economy Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Alex Midkiff (Winged Outlaw) | DNS | - | - | 3rd | | Alex Midkiff (Non-Wing Outlaw) | 8th (DNF) | - | 5th | - |
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| 12/17/2021 | Wayne County Speedway - Wayne City, IL Jason Leffler Memorial Prelim - DuQuoin Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Alex Midkiff (Winged Outlaw) | 5th | - | - | - | | Alex Midkiff (Non-Wing Outlaw) | 8th | - | - | - |
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| 12/18/2021 | Wayne County Speedway - Wayne City, IL Jason Leffler Memorial - DuQuoin Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Alex Midkiff (Winged Outlaw) | - | - | - | 5th | | Alex Midkiff (Non-Wing Outlaw) | - | - | - | 18th |
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