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| 6/19/2021 | Ogilvie Raceway - Ogilvie, MN Davey Tabor Memorial [Non-MSTS points] 360 Sprints - Winged: Midwest Sprint Touring Series with Midwest Power Series Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Vintage Modifieds: Northern Vintage Stockcar Racers Winged Sprints, Winged A-Class, Non-Winged Sprints, Vintage Full Body Stock Cars, WISSOTA Hornet | Results | | Dennis Olson (Vintage Modifieds) | 5th | - | - | 4th |
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| 6/25/2021 | Gondik Law Speedway - Superior, WI Limited Sprints - Winged: Upper Midwest Sprint Car Series Vintage Modifieds: Northern Vintage Stockcar Racers 360 Sprints - Non-Winged, 305 Sprints - Non-Winged, Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Dennis Olson (Vintage Modifieds) | 8th | - | - | - |
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| 7/9/2021 | Princeton Speedway - Princeton, MN Weekly races Vintage Modifieds: Northern Vintage Stockcar Racers Hobby Stocks, A Modifieds, B Modifieds, Vintage Full Body Stock Cars, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Dennis Olson (Vintage Modifieds) | 5th | - | - | 8th |
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| 7/10/2021 | North Central Speedway - Brainerd, MN Vintage Modifieds: Northern Vintage Stockcar Racers Hobby Stocks, A Modifieds, B Modifieds, Vintage Full Body Stock Cars, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Dennis Olson (Vintage Modifieds) | 6th | - | - | 2nd |
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| 7/18/2021 | Proctor Speedway - Proctor, MN AFCO ROC Qualifier + Vintage Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dennis Olson (Vintage Modifieds) | 4th | - | - | 8th |
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| 8/13/2021 | Gondik Law Speedway - Superior, WI National Suicide Prevention Lifeline Night-Pure Stock Special Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dennis Olson (Vintage Modifieds) | 4th | - | - | 4th |
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| 8/14/2021 | Hibbing Raceway - Hibbing, MN Hall of Fame Night Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dennis Olson (Vintage Modifieds) | 9th (DNF) | - | - | DNS |
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