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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 | | Jordan Clary (Winged Outlaw) | 2nd | - | - | 4th | | Jordan Clary (HART Non-Wing Micros) | 5th | - | 8th | - |
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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 | | Jordan Clary (Winged Outlaw) | 1st | - | - | 3rd | | Jordan Clary (HART Non-Wing Micros) | 5th | - | 4th | - |
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| 4/1/2023 | Doe Run Raceway - Doe Run, MO 3rd Annual Small Tire Shootout Winged Outlaw, Restricted 'A' Class, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Jordan Clary (Winged Outlaw) | 2nd | - | - | 8th |
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| 5/13/2023 | Wayne County Speedway - Wayne City, IL Spring Classic Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Jordan Clary (HART Non-Wing Micros) | 2nd | - | - | 6th |
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| 5/26/2023 | Macon Speedway - Macon, IL Cornfield Combat Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, HART Non-Wing Micros | Results | | Jordan Clary (HART Non-Wing Micros) | 8th (DNF) | - | - | - |
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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 | | Jordan Clary (Winged Outlaw) | 1st | - | - | 4th | | Jordan Clary (HART Non-Wing Micros) | 5th | - | - | 10th |
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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 | | Jordan Clary (Winged Outlaw) | 3rd | - | - | 4th | | Jordan Clary (HART Non-Wing Micros) | 6th | - | 1st | 14th |
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| 6/16/2023 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged Outlaw, Winged A-Class | Results | | Jordan Clary (Winged A-Class) | 2nd | - | 7th | - |
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| 6/17/2023 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged Outlaw, Winged A-Class, Sportsman Micros | Results | | Jordan Clary (Winged A-Class) | 3rd | - | - | 15th |
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| 6/23/2023 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets 410 Sprints - Winged, Winged Outlaw, Street Stocks | Results | | Jordan Clary (Winged Outlaw) | 3rd | - | - | 8th |
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| 6/24/2023 | Macon Speedway - Macon, IL Illinois SPEED Week Midgets: POWRi National Midgets DIRTcar UMP Modifieds, Winged Outlaw, Street Stocks | Results | | Jordan Clary (Winged Outlaw) | 1st | - | - | 5th |
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| 7/7/2023 | Macon Speedway - Macon, IL 410 Sprints - Non-Winged: USAC National Sprint Cars HART Non-Wing Micros | Results | | Jordan Clary (HART Non-Wing Micros) | 1st | - | - | 5th |
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| 7/15/2023 | Macon Speedway - Macon, IL POWRi Micros at Macon Speedway DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Jordan Clary (Winged Outlaw) | 2nd | - | - | 13th (DNF) |
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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 | | Jordan Clary (Winged Outlaw) | 1st | - | - | 3rd | | Jordan Clary (HART Non-Wing Micros) | 1st | - | - | 2nd |
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| 7/28/2023 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Winged A-Class, Stock Non-Wing | Results | | Jordan Clary (Stock Non-Wing) | 4th | - | 5th | - |
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| 7/29/2023 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Winged A-Class, Stock Non-Wing | Results | | Jordan Clary (Stock Non-Wing) | - | - | - | - |
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| 7/30/2023 | Southern Illinois Raceway - Marion, IL TSM Final Take 2 Winged Outlaw, Stock Non-Wing | Results | | Jordan Clary (Stock Non-Wing) | 7th | - | 9th | - |
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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 | | Jordan Clary (HART Non-Wing Micros) | 7th | - | 7th | - |
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| 9/8/2023 | Doe Run Raceway - Doe Run, MO Twin 20 lap Winged Outlaw Micros $750 to win, Plus all regular classes Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Jordan Clary (Winged Outlaw) | 1st | - | - | 2nd |
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| 10/7/2023 | Wayne County Speedway - Wayne City, IL Columbus Day Weekend presented Aggressive Fire Prevention Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds, Sportsman Micros, HART Non-Wing Micros | Results | | Jordan Clary (Winged Outlaw) | DNS | - | - | 8th | | Jordan Clary (HART Non-Wing Micros) | 6th | - | - | 3rd |
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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 | | Jordan Clary (Winged Outlaw) | 5th | - | - | 18th | | Jordan Clary (Non-Wing Outlaw) | 2nd | - | - | 17th | | Jordan Clary (Winged A-Class) | 4th | - | - | 5th |
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