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| 4/3/2021 | Slinger Super Speedway - Slinger, WI 2020 Awards Banquet/ 2021 Registration Asphalt Late Models, Asphalt Super Late Models, Asphalt Mini Stocks, Sportsmans, Outlaws, Pro Legends, Asphalt 4-Cylinders, Asphalt Street Stocks, Asphalt Sport Mods, Asphalt Figure 8 Stock Cars, Asphalt Sport Trucks, Sport Compact, Outlaw Hobby Stocks, Honda Challenge, Figure 8 - FWD-Open | Results | | Ben Massman (Pro Legends) | - | - | - | - |
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| 5/30/2021 | Slinger Super Speedway - Slinger, WI EH Wolf & Sons FIREWORKS!! Asphalt Super Late Models, Outlaws, Pro Legends, Asphalt 4-Cylinders, Asphalt Figure 8 Stock Cars, Sport Compact, Honda Challenge | Results | | Ben Massman (Pro Legends) | 1st | - | 6th | - |
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| 6/13/2021 | Slinger Super Speedway - Slinger, WI Keith’s Marina/Chix 4 A Cause Race Against Cancer Asphalt Late Models, Asphalt Super Late Models, Sportsmans, Outlaws, Pro Legends, Asphalt Figure 8 Stock Cars, Honda Challenge | Results | | Ben Massman (Pro Legends) | 4th | - | - | 11th |
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| 7/11/2021 | Slinger Super Speedway - Slinger, WI Small Car Nationals Asphalt Mini Stocks, Outlaws, Pro Legends, Asphalt 4-Cylinders, Asphalt Sport Trucks, Muscle Car, Sport Compact, Honda Challenge, Figure 8 - FWD-Open | Results | | Ben Massman (Pro Legends) | 4th | - | - | 13th (DNF) |
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| 7/23/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing Hobby Stocks, Sportsmans, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Ben Massman (Masters Legends) | 7th | - | - | 13th |
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| 7/30/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing - COPS Night Hobby Stocks, Sportsmans, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Ben Massman (Masters Legends) | 3rd | - | - | 10th |
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| 8/22/2021 | Slinger Super Speedway - Slinger, WI Memorial Go-Kart Tribute Night Asphalt Late Models, Pro Legends, Asphalt Street Stocks, Sport Compact, Figure 8 - FWD-Open | Results | | Ben Massman (Pro Legends) | 3rd | - | - | 7th |
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| 9/12/2021 | Slinger Super Speedway - Slinger, WI Championship Sunday Asphalt Late Models, Asphalt Mini Stocks, Outlaws, Pro Legends, Asphalt 4-Cylinders, Asphalt Figure 8 Stock Cars, Muscle Car | Results | | Ben Massman (Pro Legends) | 4th | - | - | - |
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