| | Heat | Dash | B Feature | A Feature |
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| 2/26/2021 | Southern Illinois Center - Duquoin, IL Midwest Winter Nationals Non-Wing Outlaw | Results | | Jake Cheatham (Non-Wing Outlaw) | - | - | - | 2nd |
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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 | | Jake Cheatham (Winged Outlaw) | 5th | - | - | 9th | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | 2nd |
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| 2/27/2021 | Southern Illinois Center - Duquoin, IL Midwest Winter Nationals Non-Wing Outlaw | Results | | Jake Cheatham (Non-Wing Outlaw) | - | - | - | 20th |
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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 | | Jake Cheatham (Winged Outlaw) | 4th | - | - | 19th | | Jake Cheatham (Non-Wing Outlaw) | 4th | - | 4th | 20th |
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| 3/12/2021 | Southern Illinois Center - Duquoin, IL Midwest Winter Nationals Non-Wing Outlaw | Results | | Jake Cheatham (Non-Wing Outlaw) | - | - | - | 8th |
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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 | | Jake Cheatham (Winged Outlaw) | 5th | - | - | 8th | | Jake Cheatham (Non-Wing Outlaw) | 3rd | - | 2nd | 8th |
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| 3/13/2021 | Southern Illinois Center - Duquoin, IL Midwest Winter Nationals Non-Wing Outlaw | Results | | Jake Cheatham (Non-Wing Outlaw) | - | - | - | 14th |
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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 | | Jake Cheatham (Winged Outlaw) | 2nd | - | - | 4th | | Jake Cheatham (Non-Wing Outlaw) | 1st | - | - | 14th |
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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 | | Jake Cheatham (Winged Outlaw) | 3rd | - | - | 2nd |
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| 4/17/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Jake Cheatham (Winged Outlaw) | 1st | - | - | 1st |
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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 | | Jake Cheatham (Winged Outlaw) | 4th | - | - | 5th |
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| 5/1/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Jake Cheatham (Winged Outlaw) | 3rd | - | - | 3rd |
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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 | | Jake Cheatham (Winged Outlaw) | 1st | - | - | 1st |
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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 | | Jake Cheatham (Winged Outlaw) | 3rd | - | - | 5th | | Jake Cheatham (Non-Wing Outlaw) | 3rd | - | - | 2nd |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 3rd | - | - | 8th |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 3rd | - | - | 3rd |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | 4th |
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| 7/23/2021 | Coles County Speedway - Mattoon, IL Non Wing Hart Series Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jake Cheatham (Non-Wing Outlaw) | 3rd | - | - | 9th |
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| 7/24/2021 | Highland Speedway - Highland, IL Spectator Race DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Jake Cheatham (Winged Outlaw) | 1st | - | - | 11th |
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| 7/30/2021 | Southern Illinois Raceway - Marion, IL Prairie Farms Terry Sprague Memorial Night 1 Stock Non-Wing | Results | | Jake Cheatham (Stock Non-Wing) | 3rd | - | 2nd | 17th |
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| 7/31/2021 | Southern Illinois Raceway - Marion, IL Prairie Farms Terry Sprague Memorial Final Stock Non-Wing | Results | | Jake Cheatham (Stock Non-Wing) | 2nd | - | 9th | - |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 1st | - | - | 1st |
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| 8/15/2021 | Tri City Speedway - Granite City, IL Sunday Racing DIRTcar Sport Compact, Winged Outlaw, Winged Outlaw, Restricted Box Stock, Unrestricted Box Stock, 500 Winged Open Outlaw, Dirt Mini Late Models, LO 206 Cage Junior 1 Winged, Flat Jr. 1 Clone | Results | | Jake Cheatham (Winged Outlaw) | 2nd | - | - | 2nd |
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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 | | Jake Cheatham (Winged Outlaw) | 3rd | - | - | 11th |
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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 | | Jake Cheatham (Winged Outlaw) | 5th | - | 6th | - |
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| 9/17/2021 | Tri City Speedway - Granite City, IL Fan App & TDT Night UMP LM, Mods St Stk & 4-cyl with BMods, Winged Micros & Kids Power Wheels DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Winged Outlaw, B Modifieds, Street Stocks | Results | | Jake Cheatham (Winged Outlaw) | 2nd | - | - | 2nd |
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| 9/18/2021 | Highland Speedway - Highland, IL Championship NIght DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Jake Cheatham (Winged Outlaw) | 3rd | - | - | 5th |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 5th | - | - | 16th (DNF) |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 1st | 6th | - | 4th |
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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 | | Jake Cheatham (Winged Outlaw) | 2nd | - | - | - | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | - |
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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 | | Jake Cheatham (Winged Outlaw) | - | - | - | 3rd | | Jake Cheatham (Non-Wing Outlaw) | - | - | - | 4th |
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