| | Heat | Dash | B Feature | A Feature |
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| 5/13/2023 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros, HART Non-Wing Micros | Results | | Larry Drake (Winged Outlaw) | 7th (DNF) | - | - | DNS |
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| 6/9/2023 | Coles County Speedway - Mattoon, IL Eastern Illinois Weekend #1 Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Adult Open, HART Non-Wing Micros | Results | | Larry Drake (Winged Outlaw) | 1st | - | - | 1st |
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| 6/16/2023 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged Outlaw, Winged A-Class | Results | | Larry Drake (Winged A-Class) | 7th | - | 15th | - |
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| 6/17/2023 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged Outlaw, Winged A-Class, Sportsman Micros | Results | | Larry Drake (Winged A-Class) | 7th | - | - | - |
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| 7/14/2023 | Coles County Speedway - Mattoon, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Adult Open, HART Non-Wing Micros | Results | | Larry Drake (Winged Outlaw) | 1st | - | - | 1st | | Larry Drake (HART Non-Wing Micros) | 2nd | - | - | 2nd |
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| 7/15/2023 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros, HART Non-Wing Micros | Results | | Larry Drake (Winged Outlaw) | 5th | - | - | 9th (DNF) |
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| 8/5/2023 | Wayne County Speedway - Wayne City, IL Faster Saturday Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Larry Drake (Winged Outlaw) | 3rd | - | - | DNS |
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| 9/2/2023 | Coles County Speedway - Mattoon, IL Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, HART Non-Wing Micros | Results | | Larry Drake (Winged Outlaw) | - | - | - | - | | Larry Drake (HART Non-Wing Micros) | 2nd | - | - | 1st |
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| 9/23/2023 | Coles County Speedway - Mattoon, IL Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Adult Open, HART Non-Wing Micros | Results | | Larry Drake (HART Non-Wing Micros) | 1st | - | - | 2nd |
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| 10/21/2023 | Coles County Speedway - Mattoon, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Larry Drake (Winged Outlaw) | 1st | - | - | 2nd | | Larry Drake (Non-Wing Outlaw) | 5th | - | 1st | 21st (DNF) |
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