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| 4/7/2019 | Slinger Super Speedway - Slinger, WI Sunday Afternoon Open Day Asphalt Late Models, Asphalt Super Late Models, Asphalt Mini Stocks, Sportsmans, Outlaws, Pro Legends, Asphalt 4-Cylinders, Asphalt Figure 8 Stock Cars, Sport Compact, Super Stocks, Generic 2, Honda Challenge | Results | | Dirk Henry (Pro Legends) | - | - | - | - |
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| 5/25/2019 | Dells Raceway Park - Wisconsin Dells, WI CWRA Nabbefeldt Memorial Twin 55 lap Super Late Model Features / SS&E Pure Stock Triple Crown Race#1 Pro Legends, Asphalt Sportsman Late Models, Asphalt Sport Mods, Asphalt Pure Stocks | Results | | Dirk Henry (Pro Legends) | - | 6th | - | 6th |
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| 5/26/2019 | Slinger Super Speedway - Slinger, WI EH Wolf Memorial Day Village of Slinger 150 Asphalt Late Models, Asphalt Super Late Models, Outlaws, Pro Legends, Asphalt 4-Cylinders, Asphalt Figure 8 Stock Cars, Super Stocks, Honda Challenge | Results | | Dirk Henry (Pro Legends) | 2nd | - | - | 6th |
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| 6/1/2019 | Elko Speedway - Elko, MN NASCAR Asphalt Late Models, Hobby Stocks, Street Stocks, Bandits, Masters Legends | Results | | Dirk Henry (Masters Legends) | - | - | - | 11th |
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| 7/27/2019 | Dells Raceway Park - Wisconsin Dells, WI INEX Regional Event Asphalt Late Models, Midwest Modifieds, Pro Legends, Asphalt Sportsman Late Models | Results | | Dirk Henry (Pro Legends) | 5th | - | - | 2nd |
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| 8/24/2019 | Elko Speedway - Elko, MN NASCAR Asphalt Late Models, Hobby Stocks, Street Stocks, Bandits, Masters Legends | Results | | Dirk Henry (Masters Legends) | - | - | - | 18th (DNF) |
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| 9/14/2019 | Elko Speedway - Elko, MN Late Model and Bandolero Championship Asphalt Late Models, Hobby Stocks, Street Stocks, Bandits, Masters Legends | Results | | Dirk Henry (Masters Legends) | - | - | - | 5th |
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| 9/21/2019 | Elko Speedway - Elko, MN Thunderstruck/Thunder car championship night Asphalt Late Models, Hobby Stocks, Street Stocks, Masters Legends, WISSOTA Midwest Mods | Results | | Dirk Henry (Masters Legends) | - | - | - | 4th |
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