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| 3/3/2023 | Wayne County Speedway - Wayne City, IL Midwest Winter Nationals Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Drew Sherman (Winged A-Class) | 7th | - | - | 9th | | Drew Sherman (Stock Non-Wing) | 2nd | - | - | 18th | | Drew Sherman (HART Non-Wing Micros) | 3rd | - | - | 11th |
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| 3/4/2023 | Wayne County Speedway - Wayne City, IL Midwest Winter Nationals Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Drew Sherman (Winged A-Class) | 3rd | - | - | 4th | | Drew Sherman (Stock Non-Wing) | 5th | - | 1st | 20th | | Drew Sherman (HART Non-Wing Micros) | 7th | - | 8th | - |
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| 3/10/2023 | Wayne County Speedway - Wayne City, IL Season Opener Non-Wing Outlaw, Junior Sprints | Results | | Drew Sherman (Non-Wing Outlaw) | 5th | - | - | 8th |
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| 3/11/2023 | Wayne County Speedway - Wayne City, IL Xtreme Outlaw Series National Midgets Non-Wing Outlaw, Junior Sprints | Results | | Drew Sherman (Non-Wing Outlaw) | 6th | - | - | 8th |
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| 6/2/2023 | Wayne County Speedway - Wayne City, IL Xtreme Outlaw Midgets Midgets: Xtreme Outlaw Midgets Winged Outlaw, Restricted 'A' Class, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Drew Sherman (HART Non-Wing Micros) | 7th | - | - | 15th |
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| 6/3/2023 | Wayne County Speedway - Wayne City, IL Xtreme Outlaw Midgets Midgets: Xtreme Outlaw Midgets Winged Outlaw, Restricted 'A' Class, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Drew Sherman (HART Non-Wing Micros) | 7th | - | 5th | - |
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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 | | Drew Sherman (Winged A-Class) | 2nd | - | - | 6th (DNF) | | Drew Sherman (Stock Non-Wing) | 3rd | - | - | 3rd |
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| 6/17/2023 | Wayne County Speedway - Wayne City, IL Weekly Event Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Drew Sherman (Winged A-Class) | 2nd | - | - | 3rd | | Drew Sherman (HART Non-Wing Micros) | 6th | - | - | 12th |
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| 6/27/2023 | Miami County Raceway - Peru, IN Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, HART Non-Wing Micros, Senior Micros | Results | | Drew Sherman (Winged A-Class) | 5th | - | - | 2nd | | Drew Sherman (Stock Non-Wing) | 4th | - | - | 6th |
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| 7/16/2023 | Wayne County Speedway - Wayne City, IL Sunday Summer Sizzle Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Drew Sherman (Winged A-Class) | 1st | - | - | 2nd | | Drew Sherman (HART Non-Wing Micros) | 8th | - | - | 6th |
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| 8/18/2023 | Wayne County Speedway - Wayne City, IL Jason Leffler Memorial Midgets, Winged Outlaw, Restricted 'A' Class, Junior Sprints, HART Non-Wing Micros | Results | | Drew Sherman (HART Non-Wing Micros) | 6th | - | 10th | - |
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| 8/19/2023 | Wayne County Speedway - Wayne City, IL Dan Robinson Memorial Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Lightning Sprints, HART Non-Wing Micros | Results | | Drew Sherman (Winged A-Class) | 3rd | - | - | 11th | | Drew Sherman (HART Non-Wing Micros) | 2nd | - | 9th | - |
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| 8/26/2023 | US 24 Speedway - Logansport, IN POINT NIGHT #9 RED BARN FIREARMS NOW600 SENIOR $500, CONCEPT CHASSIS NOW600 A WING $500 TO WIN Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, HART Non-Wing Micros, Senior Micros | Results | | Drew Sherman (Winged A-Class) | 7th | - | - | 8th | | Drew Sherman (Stock Non-Wing) | 6th | - | 3rd | - |
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| 11/4/2023 | Wayne County Speedway - Wayne City, IL Fall Spectacular Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Drew Sherman (Winged A-Class) | 1st | - | - | 1st | | Drew Sherman (HART Non-Wing Micros) | 6th | - | - | 9th |
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