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| 5/18/2019 | Oakshade Raceway - Wauseon, OH Full Show DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 1st | - | - | 4th |
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| 6/8/2019 | Oakshade Raceway - Wauseon, OH Wallace Racing Products DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 6th | - | - | 9th |
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| 6/22/2019 | Oakshade Raceway - Wauseon, OH Night of Wheels DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 2nd | - | - | 1st |
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| 6/29/2019 | Oakshade Raceway - Wauseon, OH Oakshade/Attica LM Challenge DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 2nd | - | - | 8th |
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| 7/6/2019 | Oakshade Raceway - Wauseon, OH American Vintage Cars DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 11th | - | - | 7th |
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| 7/20/2019 | Oakshade Raceway - Wauseon, OH Full Show DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 5th | - | - | 8th |
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| 7/27/2019 | Oakshade Raceway - Wauseon, OH 30th Annual Barney Oldfield/ALMS DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 4th | - | - | 7th |
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| 8/3/2019 | Oakshade Raceway - Wauseon, OH Full Show DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 2nd | - | - | 1st |
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| 8/10/2019 | Oakshade Raceway - Wauseon, OH Central Collison Night/BOSS Sprints 410 Sprints - Non-Winged: BOSS Buckeye Outlaw Sprint Series DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Non-Winged Sprints, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 1st | - | - | 7th |
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| 8/24/2019 | Oakshade Raceway - Wauseon, OH Wauseon Machine & Manufacturing Night DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 4th | - | - | 7th |
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| 8/31/2019 | Oakshade Raceway - Wauseon, OH Cricket Wireless Night- ALMS DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 4th | - | - | 6th |
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| 9/7/2019 | Oakshade Raceway - Wauseon, OH DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 7th | - | - | 19th |
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| 9/14/2019 | Oakshade Raceway - Wauseon, OH Season Championship Night DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 2nd | - | - | 2nd |
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| 9/21/2019 | Oakshade Raceway - Wauseon, OH Papa Boiler Bomber Spectacular DIRTcar Late Models, DIRTcar Sportsmans, Factory Stocks, Sport Compact | Results | | Bob Gregory (DIRTcar Sportsmans) | 2nd | - | - | 14th |
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