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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 | | Jaylon Mills (Winged Outlaw) | 2nd | - | - | 4th |
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| 4/15/2023 | Wayne County Speedway - Wayne City, IL Season Opener Winged Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Jaylon Mills (Winged Outlaw) | 3rd | - | - | 5th |
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| 5/6/2023 | Coles County Speedway - Mattoon, IL Non Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Adult Open, HART Non-Wing Micros | Results | | Jaylon Mills (HART Non-Wing Micros) | 1st | - | - | 1st |
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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 | | Jaylon Mills (Winged Outlaw) | 4th | - | - | 9th | | Jaylon Mills (HART Non-Wing Micros) | 4th | - | - | 12th |
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| 5/20/2023 | 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 | | Jaylon Mills (Winged Outlaw) | 1st | - | - | 1st | | Jaylon Mills (HART Non-Wing Micros) | 4th | - | - | 11th |
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| 5/27/2023 | Southern Illinois Raceway - Marion, IL Maier's Tidy Bowl Dwarf Special Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros, HART Non-Wing Micros | Results | | Jaylon Mills (Winged Outlaw) | 1st | - | - | 4th | | Jaylon Mills (Non-Wing Outlaw) | 8th (DNF) | - | - | DNS |
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| 5/28/2023 | Brownstown Bullring - Brownstown, IL Willy's Carburetor Night at the Races DIRTcar UMP Modifieds, Factory Stocks, Limited Modified, DIRTcar 4 Cylinders, HART Non-Wing Micros | Results | | Jaylon Mills (HART Non-Wing Micros) | 2nd | - | - | 4th |
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| 5/29/2023 | Brownstown Bullring - Brownstown, IL Mullins Race Engines Night at the Races DIRTcar UMP Modifieds, Factory Stocks, Limited Modified, DIRTcar 4 Cylinders, HART Non-Wing Micros | Results | | Jaylon Mills (HART Non-Wing Micros) | 4th | - | - | 6th |
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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 | | Jaylon Mills (HART Non-Wing Micros) | 1st | - | - | 13th |
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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 | | Jaylon Mills (Winged Outlaw) | 6th | - | - | 1st | | Jaylon Mills (HART Non-Wing Micros) | 4th | - | 3rd | - |
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| 6/10/2023 | 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 | | Jaylon Mills (Winged Outlaw) | 7th | - | - | 15th |
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| 6/16/2023 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged Outlaw, Winged A-Class | Results | | Jaylon Mills (Winged A-Class) | 5th | - | 4th | 17th |
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| 6/17/2023 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged Outlaw, Winged A-Class, Sportsman Micros | Results | | Jaylon Mills (Winged A-Class) | 2nd | - | - | - |
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| 6/23/2023 | Doe Run Raceway - Doe Run, MO $750 30lap Winged Outlaw micro plus Fireworks Show by Harris Wholesale Fireworks makeup features Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Jaylon Mills (Winged Outlaw) | 1st | - | - | 2nd |
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| 7/7/2023 | Macon Speedway - Macon, IL 410 Sprints - Non-Winged: USAC National Sprint Cars HART Non-Wing Micros | Results | | Jaylon Mills (HART Non-Wing Micros) | 3rd | - | - | 1st |
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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 | | Jaylon Mills (Winged Outlaw) | 7th | - | - | 7th | | Jaylon Mills (HART Non-Wing Micros) | 2nd | - | - | 2nd |
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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 | | Jaylon Mills (Winged Outlaw) | 2nd | - | - | 1st | | Jaylon Mills (HART Non-Wing Micros) | 4th | - | - | 1st |
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| 7/28/2023 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Winged A-Class, Stock Non-Wing | Results | | Jaylon Mills (Stock Non-Wing) | 5th | - | 18th (DNF) | - |
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| 7/29/2023 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Winged A-Class, Stock Non-Wing | Results | | Jaylon Mills (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 | | Jaylon Mills (Stock Non-Wing) | 5th | - | - | - |
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| 8/4/2023 | Wayne County Speedway - Wayne City, IL Fast Friday Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Jaylon Mills (Winged Outlaw) | 4th | - | - | DNS | | Jaylon Mills (HART Non-Wing Micros) | 3rd | - | - | 6th |
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| 8/12/2023 | Wayne County Speedway - Wayne City, IL Saturday Speed Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds, HART Non-Wing Micros | Results | | Jaylon Mills (HART Non-Wing Micros) | 3rd | - | - | 2nd |
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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 | | Jaylon Mills (HART Non-Wing Micros) | 4th | - | - | 13th |
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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 | | Jaylon Mills (HART Non-Wing Micros) | 5th | - | - | 15th |
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| 9/1/2023 | Doe Run Raceway - Doe Run, MO Spartan Transportation Outlaw Winged Nationals Winged Outlaw, Restricted 'A' Class, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts | Results | | Jaylon Mills (Winged Outlaw) | - | - | - | - |
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| 9/2/2023 | Doe Run Raceway - Doe Run, MO Spartan Transportation Outlaw Winged Nationals Winged Outlaw, Restricted 'A' Class, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts | Results | | Jaylon Mills (Winged Outlaw) | 5th | - | 4th | 13th |
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| 9/6/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO KKM Challenge Race Practice Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Jaylon Mills (Non-Wing Outlaw) | - | - | - | - |
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| 9/7/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO KKM Challenge Race Non-Wing Outlaw: POWRi 600cc Outlaw Micro Sprints Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jaylon Mills (Non-Wing Outlaw) | 5th | - | 5th | - |
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| 9/8/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO KKM Challenge Race Non-Wing Outlaw: POWRi 600cc Outlaw Micro Sprints Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jaylon Mills (Non-Wing Outlaw) | 4th | - | 3rd | 21st |
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| 9/9/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO KKM Challenge Race - POWRi Non-Wing $10,000.00 to WIN Non-Wing Outlaw: POWRi 600cc Outlaw Micro Sprints Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jaylon Mills (Non-Wing Outlaw) | - | - | 4th | 14th |
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| 9/30/2023 | 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 | | Jaylon Mills (HART Non-Wing Micros) | 4th | - | - | 4th |
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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 | | Jaylon Mills (Winged Outlaw) | 3rd | - | - | 7th | | Jaylon Mills (HART Non-Wing Micros) | 7th | - | - | 4th |
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| 10/14/2023 | Tri-State Speedway - Haubstadt, IN The Harvest Cup 410 Sprints - Non-Winged: Midwest Sprint Car Series MSCS Lightning Sprints: Midwest Mini Sprint Association | Results | | Jaylon Mills (Lightning Sprints) | 2nd | - | - | 18th |
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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 | | Jaylon Mills (Winged Outlaw) | 5th | - | 1st | 19th | | Jaylon Mills (Non-Wing Outlaw) | 1st | - | - | 20th |
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| 12/26/2023 | Tulsa Expo Raceway - Tulsa, OK Shootout Parking / Check-In Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Jaylon Mills (Winged Outlaw) | - | - | - | - | | Jaylon Mills (Non-Wing Outlaw) | - | - | - | - | | Jaylon Mills (Stock Non-Wing) | - | - | - | - |
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| 12/27/2023 | Tulsa Expo Raceway - Tulsa, OK Morning Practice Then Racing Winged Outlaw: Tulsa Shootout | Results | | Jaylon Mills (Winged Outlaw) | 7th | - | - | - |
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| 12/28/2023 | Tulsa Expo Raceway - Tulsa, OK Racing - Day 2 Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jaylon Mills (Winged Outlaw) | - | - | - | - | | Jaylon Mills (Non-Wing Outlaw) | 2nd | - | - | - |
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| 12/30/2023 | Tulsa Expo Raceway - Tulsa, OK Racing - Day 4 Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Jaylon Mills (Winged Outlaw) | - | - | - | - | | Jaylon Mills (Non-Wing Outlaw) | - | 8th | - | - |
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| 12/31/2023 | Tulsa Expo Raceway - Tulsa, OK It's Driller Time! Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Jaylon Mills (Winged Outlaw) | - | - | - | - | | Jaylon Mills (Non-Wing Outlaw) | - | - | - | - |
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