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| 8/7/2021 | Monadnock Speedway - Winchester, NH NHSTRA Modified 100 & Six Shooters Asphalt Late Models, Factory Stocks, Asphalt Mini Stocks, Hobby Stocks, A Modifieds, Street Stocks | Results | | Caleb Cashman (Asphalt Late Models) | 8th | - | - | 14th |
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| 8/14/2021 | Monadnock Speedway - Winchester, NH Tri Track Modified 100 Asphalt Late Models, Factory Stocks, Asphalt Mini Stocks, A Modifieds, Asphalt Small Block Modifieds, Pure Stock | Results | | Caleb Cashman (Asphalt Late Models) | 7th | - | - | 12th |
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| 8/28/2021 | Monadnock Speedway - Winchester, NH Street Stock Battle for The Belt Championship Asphalt Late Models, Factory Stocks, Asphalt Mini Stocks, Street Stocks, Asphalt Stock Cars, Pure Stock | Results | | Caleb Cashman (Asphalt Late Models) | 4th | - | - | 9th |
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| 9/4/2021 | Monadnock Speedway - Winchester, NH Pro 4 Modifieds Paul Roach Memorial Event Asphalt Late Models, Factory Stocks, A Modifieds, Street Stocks, Pure Stock | Results | | Caleb Cashman (Asphalt Late Models) | 7th | - | - | 7th |
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| 9/18/2021 | Monadnock Speedway - Winchester, NH Whitcomb 125 Championship presented by Milton Cat Asphalt Late Models, Factory Stocks, Asphalt Mini Stocks, A Modifieds, Street Stocks, Enduro, Pure Stock | Results | | Caleb Cashman (Asphalt Late Models) | 9th | - | - | 18th |
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