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| 6/13/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Jake Cheatham (Winged Outlaw) | 5th | - | - | 16th (DNF) | | Jake Cheatham (Stock Non-Wing) | 6th | - | - | 7th |
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| 6/19/2020 | Miami County Raceway - Peru, IN Fast Friday Featuring the HART Series Non-Wing Outlaw, Restricted Non Winged Micros, Stock Non-Wing, 125cc Winged Micros, 125cc Non Winged Micros, 270 Winged Micros | Results | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | 2nd |
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| 6/20/2020 | Miami County Raceway - Peru, IN HART Series Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros | Results | | Jake Cheatham (Non-Wing Outlaw) | 3rd | - | - | 6th |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 4th | - | - | 1st |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | 3rd |
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| 7/3/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship $20K to Win! Winged Outlaw Only Winged Outlaw | Results | | Jake Cheatham (Winged Outlaw) | 5th | - | 8th | - |
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| 7/4/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship $20K to Win! Winged Outlaw Only Winged Outlaw | Results | | Jake Cheatham (Winged Outlaw) | 5th | - | - | - |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | 4th |
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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 | | Jake Cheatham (Non-Wing Outlaw) | - | - | - | 1st |
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| 8/21/2020 | Wayne County Speedway - Wayne City, IL HART at Coles County Speedway Non-Wing Outlaw | Results | | Jake Cheatham (Non-Wing Outlaw) | 1st | - | - | 1st |
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| 8/22/2020 | Southern Illinois Raceway - Marion, IL Points Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Jake Cheatham (Non-Wing Outlaw) | 1st | - | - | 2nd |
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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 | | Jake Cheatham (Winged Outlaw) | 1st | - | - | 1st |
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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 | | Jake Cheatham (Winged Outlaw) | 4th | - | - | 10th |
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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 | | Jake Cheatham (Winged Outlaw) | 1st | - | - | 4th |
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| 9/11/2020 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Prelim Night Stock Non-Wing | Results | | Jake Cheatham (Stock Non-Wing) | 8th | - | - | - |
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| 9/12/2020 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Championship Night Stock Non-Wing | Results | | Jake Cheatham (Stock Non-Wing) | 6th | - | - | - |
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| 9/18/2020 | KC Raceway - Independence, MO MICRO/Points Race 11 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds, Sportsman Micros, Mod Lites | Results | | Jake Cheatham (600cc Modifieds) | 1st | - | - | 1st |
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| 9/19/2020 | 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 | | Jake Cheatham (Non-Wing Outlaw) | 1st | - | - | 1st |
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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 | | Jake Cheatham (Non-Wing Outlaw) | 6th | - | - | - |
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| 9/26/2020 | Wayne County Speedway - Wayne City, IL Trump 45 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints | Results | | Jake Cheatham (Non-Wing Outlaw) | 1st | - | - | 20th |
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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 | | Jake Cheatham (Non-Wing Outlaw) | DNS | - | 2nd | 2nd |
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| 10/17/2020 | Wayne County Speedway - Wayne City, IL Gateway Vintage Racers Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Lightning Sprints, 600cc Modifieds | Results | | Jake Cheatham (Winged Outlaw) | 1st | - | - | 12th (DNF) | | Jake Cheatham (Non-Wing Outlaw) | 2nd | - | - | 3rd |
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