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| 8/7/2021 | Willard Speedway - Willard, KY Race Day Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 2nd | - | - | 10th |
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| 8/14/2021 | Willard Speedway - Willard, KY Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Super Stocks, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 4th | - | - | 4th |
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| 8/21/2021 | Willard Speedway - Willard, KY Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 5th | - | - | 7th |
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| 8/28/2021 | Willard Speedway - Willard, KY Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 5th | - | - | 3rd |
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| 9/4/2021 | Willard Speedway - Willard, KY American Crate All-Star Series Race! DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 5th | - | - | 18th |
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| 9/11/2021 | Willard Speedway - Willard, KY Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 4th | - | - | DNS |
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| 9/18/2021 | Willard Speedway - Willard, KY Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 4th | - | - | 6th |
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| 10/2/2021 | Willard Speedway - Willard, KY Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models, Outlaw Hobby Stocks | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 4th | - | - | 10th |
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| 10/9/2021 | Willard Speedway - Willard, KY Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models, Outlaw Hobby Stocks | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 5th | - | - | 17th |
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| 10/23/2021 | Willard Speedway - Willard, KY Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models, Outlaw Hobby Stocks | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 4th | - | - | 4th |
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| 11/6/2021 | Willard Speedway - Willard, KY Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models, Outlaw Hobby Stocks | Results | | Brian Pennington (DIRTcar UMP Modifieds) | 4th | - | - | 7th |
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