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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 | | Bryan Brewster (Winged Outlaw) | 6th | - | 5th (DNF) | - |
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| 4/7/2023 | Doe Run Raceway - Doe Run, MO Reg. night all classes {if not small tire rain date Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Bryan Brewster (Winged Outlaw) | 4th | - | - | 8th |
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| 5/26/2023 | Doe Run Raceway - Doe Run, MO 3rd annual Doe Run Raceway bike giveaway + Nickel race with Gateway Vintage club Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Bryan Brewster (Winged Outlaw) | 3rd | - | - | 7th |
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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 | | Bryan Brewster (Winged Outlaw) | 7th | - | - | 7th | | Bryan Brewster (Non-Wing Outlaw) | 6th | - | - | 13th |
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| 5/31/2023 | Tri City Speedway - Granite City, IL 410 Sprints - Winged: Kubota High Limit Racing HART Non-Wing Micros | Results | | Bryan Brewster (HART Non-Wing Micros) | 7th | - | - | 8th |
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| 6/1/2023 | Tri City Speedway - Granite City, IL Xtreme Outlaw Midgets Midgets: Xtreme Outlaw Midgets DIRTcar UMP Modifieds, Junior Sprints, Restricted Box Stock, HART Non-Wing Micros, LO 206 Cage Junior 1 Winged | Results | | Bryan Brewster (HART Non-Wing Micros) | 4th | - | - | 6th |
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| 6/2/2023 | Doe Run Raceway - Doe Run, MO "Nascar Night" 3rd Annual Kids' Kart Classic plus Mod Lites $750 to win Stock Cars, Winged Outlaw, Restricted 'A' Class, B Modifieds, Junior Sprints, Restricted Box Stock, LO 206 Dirt Karts, Sport Compact, Mod Lites | Results | | Bryan Brewster (Winged Outlaw) | 6th | - | - | DNS |
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| 7/21/2023 | Doe Run Raceway - Doe Run, MO POWRi Midgets at Doe Run Raceway Midgets: POWRi National Midgets with Xtreme Outlaw Midgets Non-Wing Outlaw, Stock Non-Wing, Mod Lites, Hybrid 600cc Micros | Results | | Bryan Brewster (Stock Non-Wing) | 6th | - | DNS | - |
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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 | | Bryan Brewster (Winged Outlaw) | 3rd | - | - | 15th |
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| 9/22/2023 | Doe Run Raceway - Doe Run, MO Twin 20 lap Pro 4/Mini Stock $500 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 | | Bryan Brewster (Winged Outlaw) | 4th | - | - | 13th |
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| 10/6/2023 | Doe Run Raceway - Doe Run, MO championship night----- last points night. 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 | | Bryan Brewster (Winged Outlaw) | 3rd | - | - | 12th |
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| 12/16/2023 | DuQuoin State Fairgrounds - 1 Mile - DU QUOIN, IL Battle at the Center - Knepper 55 Midgets: POWRi National Midgets Non-Wing Outlaw: POWRi 600cc Outlaw Micro Sprints Adult Heavy | Results | | Bryan Brewster (Non-Wing Outlaw) | 3rd | - | - | 14th |
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