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| 4/19/2014 | Winston Speedway - Rothbury, MI Opening Night! Full Program- Modifieds $750 to win DIRTcar UMP Modifieds, Factory Stocks, Asphalt Mini Stocks, Stock Cars, Street Stocks, Dirt Late Models, Hornets | Results | | Drew Wilkerson (Street Stocks) | 10th (DNF) | - | - | 7th |
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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 | | Drew Wilkerson (Street Stocks) | 2nd | - | - | 11th (DNF) |
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| 5/9/2014 | I-96 Speedway - Lake Odessa, MI 360 Sprints - Winged, DIRTcar UMP Modifieds, Street Stocks, Hornets | Results | | Drew Wilkerson (Street Stocks) | 1st | - | - | 11th |
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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 | | Drew Wilkerson (Street Stocks) | 6th (DNF) | - | - | 10th |
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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 | | Drew Wilkerson (Street Stocks) | 6th (DNF) | - | - | 8th |
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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 | | Drew Wilkerson (Street Stocks) | 7th | - | - | 1st |
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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 | | Drew Wilkerson (Street Stocks) | 4th | - | - | 8th |
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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 | | Drew Wilkerson (Street Stocks) | 4th | - | - | 7th |
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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 | | Drew Wilkerson (Street Stocks) | 5th | - | - | 10th |
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| 6/22/2014 | I-96 Speedway - Lake Odessa, MI UMP DIRTcar Summernationals Hell Tour plus the Summit Racing Equipment Modifieds DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Drew Wilkerson (Street Stocks) | 4th | - | - | 8th (DNF) |
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| 6/27/2014 | I-96 Speedway - Lake Odessa, MI 360 Sprints - Winged, DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Hornets | Results | | Drew Wilkerson (Street Stocks) | 2nd | - | - | 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 | | Drew Wilkerson (Street Stocks) | 5th | - | - | 8th |
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| 7/18/2014 | Cherry Raceway - Fife Lake, MI Pizza Hut Kids Night DIRTcar Late Models, DIRTcar UMP Modifieds, Factory Stocks, Stock Cars, Street Stocks, Hornets, Lightning Sprints | Results | | Drew Wilkerson (Street Stocks) | 2nd | - | - | 3rd |
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| 7/19/2014 | Merritt Speedway - Merritt, MI Full Show DIRTcar Late Models, DIRTcar UMP Modifieds, Factory Stocks, Stock Cars, Sportsmans, Lightning Sprints, Dirt Pro Trucks | Results | | Drew Wilkerson (Factory Stocks) | 3rd | - | - | 1st |
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| 8/1/2014 | Cherry Raceway - Fife Lake, MI Hoosier Free Hat Night DIRTcar Late Models, DIRTcar UMP Modifieds, Factory Stocks, Stock Cars, Street Stocks, Hornets, Lightning Sprints | Results | | Drew Wilkerson (Factory Stocks) | 3rd | - | - | 3rd |
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| 8/2/2014 | Merritt Speedway - Merritt, MI 360 Sprints - Winged: SOD-Sprints On Dirt (360s) DIRTcar Late Models, Stock Cars, Sportsmans, Dirt Pro Trucks | Results | | Drew Wilkerson (Sportsmans) | 8th | - | - | DNS |
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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 | | Drew Wilkerson (Street Stocks) | 6th | - | - | 10th |
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