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| 6/3/2023 | Willard Speedway - Willard, KY Regular show Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Rain Out |
| 6/10/2023 | Willard Speedway - Willard, KY Jesse Dillow Memorial Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 4th | - | - | 16th |
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| 6/17/2023 | Willard Speedway - Willard, KY Pro Late Model: American All-Star Series Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 4th | - | - | 5th |
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| 7/1/2023 | Willard Speedway - Willard, KY Regular show Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 7th (DNF) | - | - | DNS |
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| 7/22/2023 | Willard Speedway - Willard, KY Meet the driver night Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 3rd | - | - | 3rd |
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| 7/29/2023 | Willard Speedway - Willard, KY Krazy Lady Cabins 40 Christmas in July Pro Late Model: American All-Star Series Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Mini Wedge, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 3rd | - | - | 7th |
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| 8/26/2023 | Mudlick Valley Raceway - Tollesboro, KY Meet the drivers!!! Dirt Super Late Models, Factory Stocks, A Modifieds, B Modifieds, Dirt Mini Stocks, 604 Crate Late Models | Results | | Brian Pennington (A Modifieds) | 4th | - | - | DNS |
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| 9/9/2023 | Thunder Mountain Speedway - Corbin, KY Ladies night & Powder Puff with 604 Crates $3,000 to win (Jr FWD) Hobby Stocks, A Modifieds, Hornets, Dirt Mini Stocks, 604 Crate Late Models | Rain Out |
| 9/16/2023 | Mudlick Valley Raceway - Tollesboro, KY 4cylinder Falltastic $1000 + $1000 to win UMP MOD Dirt Super Late Models, Factory Stocks, A Modifieds, B Modifieds, Dirt Mini Stocks, 604 Crate Late Models | Results | | Brian Pennington (A Modifieds) | 2nd | - | - | 3rd |
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| 10/14/2023 | Willard Speedway - Willard, KY Trick or Treat on The Track DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | - | - | - | 5th |
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| 11/25/2023 | 411 Motor Speedway - Seymour, TN The Leftover DIRTcar UMP Modifieds, A Modifieds, Street Stocks, Dirt Late Models, Economy Late Models, Asphalt Mini Stock, Crown Vic | Results | | Brian Pennington (A Modifieds) | - | - | 8th | - |
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