| | Heat | Dash | B Feature | A Feature |
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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 |
| 5/18/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Winged Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Winged Outlaw) | 7th | - | - | - |
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| 5/25/2019 | Southern Illinois Raceway - Marion, IL Race/Armed Forces Night/Restrictor Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Winged Outlaw) | 4th | - | - | 11th |
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| 6/21/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Colton Booten (Winged A-Class) | - | - | - | - |
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| 6/29/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Winged Outlaw) | 7th (DNF) | - | - | DNS |
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| 7/13/2019 | Southern Illinois Raceway - Marion, IL Race/Gage Besing Memorial Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Non-Wing Outlaw) | 6th | - | 7th | - |
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| 7/26/2019 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Stock Non-Wing | Results | | Colton Booten (Stock Non-Wing) | 7th | - | 14th | - |
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| 7/27/2019 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Stock Non-Wing | Results | | Colton Booten (Stock Non-Wing) | 3rd | - | 12th | - |
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| 8/3/2019 | Southern Illinois Raceway - Marion, IL Race Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Winged Outlaw) | 5th | - | - | 14th (DNF) |
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| 8/10/2019 | Southern Illinois Raceway - Marion, IL Race/Dwarf special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Winged Outlaw) | 8th (DNF) | - | - | DNS |
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| 8/23/2019 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Winged A-Class | Results | | Colton Booten (Winged A-Class) | 10th | - | 12th (DNF) | - |
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| 9/7/2019 | Southern Illinois Raceway - Marion, IL Race/Chase night 1 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Winged Outlaw) | 5th | - | - | 10th |
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| 9/14/2019 | Southern Illinois Raceway - Marion, IL Race/Chase night 2/Jerry Holder Memorial Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Winged Outlaw) | 2nd | - | - | 6th |
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| 9/21/2019 | Southern Illinois Raceway - Marion, IL Race/Chase night 3 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Winged Outlaw) | 6th | - | - | 8th |
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| 9/28/2019 | Southern Illinois Raceway - Marion, IL Race/Chase night 4 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Winged Outlaw) | 6th | - | - | 7th |
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| 10/5/2019 | Southern Illinois Raceway - Marion, IL Race/Chase Night 5 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Colton Booten (Winged Outlaw) | 9th (DNF) | - | - | 8th |
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| 10/12/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Midgets: POWRi National Midgets Winged Outlaw | Results | | Colton Booten (Winged Outlaw) | DNS | - | 12th | - |
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