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| 6/21/2014 | Winston Speedway - Rothbury, MI Bomber Special Presented by Port City Racecars DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Dakota Crain (Factory Stocks) | - | - | - | DNS |
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| 6/28/2014 | Winston Speedway - Rothbury, MI DIRTcar UMP Modifieds: Michigan Dirt Cup Modified Tour Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Dakota Crain (Factory Stocks) | DNS | - | - | 16th (DNF) |
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| 7/5/2014 | Winston Speedway - Rothbury, MI Tim Epplett Memorial for Bombers $500 to Win Presented by Holmantor Chassis DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Dakota Crain (Factory Stocks) | DNS | - | - | 16th (DNF) |
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| 7/19/2014 | Winston Speedway - Rothbury, MI Full Program DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Dakota Crain (Factory Stocks) | 8th | - | - | 9th |
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| 7/26/2014 | Winston Speedway - Rothbury, MI Kenny Blondeel Memorial for Street Stocks $500 to Win Presented by Port City Racecars DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Dakota Crain (Factory Stocks) | 7th (DNF) | - | - | 12th |
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| 8/2/2014 | Winston Speedway - Rothbury, MI Race Fans vs. Cancer Night / Michigan Auto Racing Fan Club Night DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Dakota Crain (Factory Stocks) | 8th (DNF) | - | - | 14th (DNF) |
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| 8/9/2014 | Winston Speedway - Rothbury, MI Fan Appreciation Night DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Dakota Crain (Factory Stocks) | 7th | - | - | 15th (DNF) |
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| 8/23/2014 | Winston Speedway - Rothbury, MI Back to School Night DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Dakota Crain (Factory Stocks) | 6th (DNF) | - | - | DNS |
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| 8/30/2014 | Winston Speedway - Rothbury, MI Winged Outlaw Late Model Special $1200 to Win Presented by Johnny Mac's Automotive DIRTcar UMP Modifieds, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Dakota Crain (Street Stocks) | 7th | - | - | 14th (DNF) |
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