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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 | | Billy Frey (Factory Stocks) | 7th | - | - | 7th |
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| 5/10/2014 | Winston Speedway - Rothbury, MI Michigan Dirt Cup Modifieds Opening Night DIRTcar UMP Modifieds: Michigan Dirt Cup Modified Tour Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Billy Frey (Factory Stocks) | 8th | - | - | 5th |
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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 | | Billy Frey (Factory Stocks) | - | - | - | 9th |
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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 | | Billy Frey (Factory Stocks) | 5th (DNF) | - | - | 7th |
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| 6/7/2014 | Winston Speedway - Rothbury, MI Sandy Tenbrink Memorial for Bombers - Kids Night- Fun and Games Plus Bicycle Give Aways & More DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Billy Frey (Factory Stocks) | 7th | - | - | 7th |
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| 6/14/2014 | Winston Speedway - Rothbury, MI Sunoco American Late Model Series (A.L.M.S) $2500 to Win Presented by Landrum Springs DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Billy Frey (Factory Stocks) | 7th | - | - | 9th |
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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 | | Billy Frey (Factory Stocks) | - | - | - | 12th (DNF) |
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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 | | Billy Frey (Factory Stocks) | 7th (DNF) | - | - | 10th |
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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 | | Billy Frey (Factory Stocks) | 4th | - | - | 14th (DNF) |
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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 | | Billy Frey (Factory Stocks) | 7th | - | - | 7th |
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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 | | Billy Frey (Factory Stocks) | 10th (DNF) | - | - | 6th |
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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 | | Billy Frey (Factory Stocks) | 3rd | - | - | 4th |
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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 | | Billy Frey (Factory Stocks) | 2nd | - | - | 12th (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 | | Billy Frey (Factory Stocks) | 4th | - | - | 8th |
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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 | | Billy Frey (Factory Stocks) | 5th | - | - | 14th |
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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 | | Billy Frey (Street Stocks) | DNS | - | - | 13th |
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