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| 2/23/2019 | Tri City Speedway - Granite City, IL Tri City Awards Banquet DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Jake Cheatham (Winged Outlaw) | - | - | - | - |
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| 4/13/2019 | Macon Speedway - Macon, IL 74th Season Opener / Driver - Sponsor Appreciation Photos and Autographs DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Jake Cheatham (Winged A-Class) | 3rd | - | - | 7th |
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| 5/10/2019 | Belle-Clair Speedway - Belleville, IL Midwest Season Opener Midgets: POWRi National Midgets with POWRi Winged Outlaw, B Modifieds | Results | | Jake Cheatham (Winged Outlaw) | 6th | - | 7th | - |
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| 5/11/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Rain Out |
| 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 | | Jake Cheatham (Winged Outlaw) | 4th | - | - | 20th |
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| 5/18/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Winged Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Jake Cheatham (Winged Outlaw) | 1st | - | 2nd | 18th |
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| 5/25/2019 | Wayne County Speedway - Wayne City, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Lightning Sprints | Results | | Jake Cheatham (Winged Outlaw) | 3rd | - | - | 7th | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | 4th |
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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 | | Jake Cheatham (Winged Outlaw) | 6th | - | 1st | 11th |
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| 6/1/2019 | Wayne County Speedway - Wayne City, IL USAC Regional Event/HART Non-Wing Micros Midgets, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | 3rd |
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| 6/13/2019 | Brownstown Bullring - Brownstown, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Jake Cheatham (Winged Outlaw) | 6th | - | 1st | 9th |
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| 6/14/2019 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Jake Cheatham (Winged Outlaw) | 1st | - | - | - |
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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 | | Jake Cheatham (Winged A-Class) | 1st | - | - | 1st |
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| 7/6/2019 | Coles County Speedway - Mattoon, IL Weekly Race Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jake Cheatham (Winged Outlaw) | 1st | - | - | - | | Jake Cheatham (Non-Wing Outlaw) | 3rd | - | - | - |
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| 7/11/2019 | Wayne County Speedway - Wayne City, IL Wayne County Fair Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Lightning Sprints | Results | | Jake Cheatham (Winged Outlaw) | 1st | - | - | 1st | | Jake Cheatham (Non-Wing Outlaw) | 1st | - | - | 8th |
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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 | | Jake Cheatham (Winged A-Class) | 1st | - | - | 2nd |
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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 | | Jake Cheatham (Winged Outlaw) | 4th | - | - | 6th |
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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 | | Jake Cheatham (Winged Outlaw) | 1st | - | - | 6th |
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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 | | Jake Cheatham (Winged A-Class) | 1st | - | - | 1st |
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| 8/2/2019 | Belle-Clair Speedway - Belleville, IL The Talker Guy 100 DIRTcar Late Models, DIRTcar Factory Stock, DIRTcar Sport Compact, Winged A-Class, B Modifieds | Results | | Jake Cheatham (Winged A-Class) | 1st | - | - | 2nd |
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| 8/3/2019 | Wayne County Speedway - Wayne City, IL Jr Sprint Wing/Non Wing Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints | Results | | Jake Cheatham (Winged Outlaw) | 1st | - | - | 2nd | | Jake Cheatham (Non-Wing Outlaw) | 1st | - | - | 3rd |
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| 8/9/2019 | Tri City Speedway - Granite City, IL "Driver FREE Pit Pass" UMP LM /UMP Mods/B-Mods/UMP CLM/ St. Stocks/600cc Winged Micros/Kidz Modz DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Jake Cheatham (Winged Outlaw) | 2nd | - | - | 4th |
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| 8/16/2019 | Coles County Speedway - Mattoon, IL AMSA $2500 to win Outlaw Non-Wing Night 1 Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | - |
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| 8/17/2019 | Coles County Speedway - Mattoon, IL AMSA $2500 to win Outlaw Non-Wing Night 2 Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jake Cheatham (Non-Wing Outlaw) | - | - | - | - |
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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 | | Jake Cheatham (Winged A-Class) | 3rd | - | - | 4th |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 1st | - | - | 2nd |
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| 9/1/2019 | Wayne County Speedway - Wayne City, IL HART Non-Wing Sprints at Jacksonville Speedway Non-Wing Outlaw | Results | | Jake Cheatham (Non-Wing Outlaw) | 3rd | - | - | 3rd |
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| 9/13/2019 | Tri City Speedway - Granite City, IL "Fan Appreciation Night" UMP LM/UMP Mods/B-Mods/UMP Crate LM/UMP St. Stocks/Non-Wing Micros DIRTcar Late Models, DIRTcar UMP Modifieds, Non-Wing Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | 2nd |
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| 9/20/2019 | Tri City Speedway - Granite City, IL Season Championship - UMP Late Models/UMP Modifieds/B-Modifieds/UMP Crate LM/UMP St. Stocks/Micros DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Jake Cheatham (Winged Outlaw) | 1st | - | - | 11th |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 3rd | - | - | 8th |
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| 10/5/2019 | Wayne County Speedway - Wayne City, IL Fall Non-Wing Brawl w/ HART Non-Wing Micros Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Jake Cheatham (Non-Wing Outlaw) | 3rd | - | - | 7th |
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