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| 4/26/2014 | Winston Speedway - Rothbury, MI 8th Annual Allstar Performance 50 – Sunoco American Late Model Series - $2500 to Win! DIRTcar Late Models, DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Bob Bray (Dirt Late Models) | 6th | - | - | DNS |
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| 5/3/2014 | Winston Speedway - Rothbury, MI Best appearing car awards for each class. Late Models sponsored by Sprague Auto Part DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Bob Bray (Dirt Late Models) | 6th | - | - | 11th (DNF) |
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| 5/17/2014 | Winston Speedway - Rothbury, MI Bomber Special - Presented by Port City Race Cars DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Bob Bray (Dirt Late Models) | 10th (DNF) | - | 12th (DNF) | - |
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| 5/24/2014 | Winston Speedway - Rothbury, MI Scout Night- All Scouts in uniform admitted FREE! DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Bob Bray (Dirt Late Models) | DNS | - | - | 8th (DNF) |
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| 5/31/2014 | Winston Speedway - Rothbury, MI FULL PROGRAM DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Bob Bray (Dirt Late Models) | 6th | - | - | 11th |
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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 | | Bob Bray (Dirt Late Models) | 6th | - | - | 7th |
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| 7/12/2014 | Winston Speedway - Rothbury, MI Warrior Special $300 to win Presented by APS Performance DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Bob Bray (Dirt Late Models) | 9th (DNF) | - | - | 6th |
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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 | | Bob Bray (Dirt Late Models) | DNS | - | - | DNS |
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