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| 5/8/2021 | Oswego Speedway - Oswego, NY Helena-Agri Enterprises 70th Season Kickoff Supermodifieds, 360 Supermodifieds, 100 Supermodifieds Non Winged | Results | | Dennis Rupert (100 Supermodifieds Non Winged) | 4th | - | - | 12th |
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| 5/15/2021 | Oswego Speedway - Oswego, NY Oswego County Media Group Classic Tune-Up Supermodifieds, 360 Supermodifieds, 100 Supermodifieds Non Winged | Results | | Dennis Rupert (100 Supermodifieds Non Winged) | 4th | - | - | 9th |
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| 5/27/2021 | Oswego Speedway - Oswego, NY 64th Annual CLASSIC WEEK - Open Practice Supermodifieds, 360 Supermodifieds, 100 Supermodifieds Non Winged | Results | | Dennis Rupert (100 Supermodifieds Non Winged) | - | - | - | - |
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| 5/29/2021 | Oswego Speedway - Oswego, NY 64th Annual CLASSIC WEEK - Classic Saturday Supermodifieds, 360 Supermodifieds, 100 Supermodifieds Non Winged | Results | | Dennis Rupert (100 Supermodifieds Non Winged) | - | - | - | 8th |
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| 6/19/2021 | Oswego Speedway - Oswego, NY Burke's Do It Best Homecenter and Compass Credit Union Novelis Supermodified Twin 35's Supermodifieds, 360 Supermodifieds, 100 Supermodifieds Non Winged | Results | | Dennis Rupert (100 Supermodifieds Non Winged) | 5th | - | - | 8th |
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| 7/3/2021 | Oswego Speedway - Oswego, NY Century 21 Independence Spectacular - Shampine/White Memorials, 350's - FAN CAN CHASE AND FIREWORKS! Supermodifieds, 360 Supermodifieds, 100 Supermodifieds Non Winged | Results | | Dennis Rupert (100 Supermodifieds Non Winged) | 6th | - | - | 7th |
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| 7/10/2021 | Oswego Speedway - Oswego, NY CME Electrical Summer Championship - Double Features for Supermodifieds, SBS PLUS Vintage Cars Supermodifieds, 100 Supermodifieds Non Winged | Results | | Dennis Rupert (100 Supermodifieds Non Winged) | 3rd | - | - | 10th |
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| 8/7/2021 | Oswego Speedway - Oswego, NY JP Jewelers 'Retro Night' - AUTOGRAPH SESSION! Supermodifieds, 360 Supermodifieds, 100 Supermodifieds Non Winged | Results | | Dennis Rupert (100 Supermodifieds Non Winged) | 4th | - | - | 5th |
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| 8/14/2021 | Oswego Speedway - Oswego, NY Barlow's Concessions and A&P Auto Parts Night - Supers, SBS, New York Super Stocks Supermodifieds, Asphalt Street Stocks, 100 Supermodifieds Non Winged | Results | | Dennis Rupert (100 Supermodifieds Non Winged) | 4th | - | - | 17th |
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