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| 5/26/2023 | I-94 Speedway - Fergus Falls, MN Driver Meet and Greet Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | Results | | Charles Olson (WISSOTA Late Model) | 7th (DNF) | - | - | 10th |
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| 5/27/2023 | Hibbing Raceway - Hibbing, MN Lisa Vajdl Tribute Race WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 6th | - | - | 17th (DNF) |
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| 6/4/2023 | Proctor Speedway - Proctor, MN Vintage Racers Picnic, Meet the Drivers 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 | | Charles Olson (WISSOTA Late Model) | 3rd | - | - | 7th |
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| 6/9/2023 | Gondik Law Speedway - Superior, WI Friday Night at the Races WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 4th | - | - | 6th |
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| 6/10/2023 | Hibbing Raceway - Hibbing, MN United Way Veteran Night WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 6th | - | - | 11th |
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| 6/30/2023 | Gondik Law Speedway - Superior, WI Great Lakes Border Battle-Night #1/Gondik Law Late Model Series WISSOTA Late Model: KME Late Model Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Charles Olson (WISSOTA Late Model) | 6th | - | 2nd | 21st (DNF) |
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| 7/1/2023 | Gondik Law Speedway - Superior, WI Great Lakes Border Battle-Night #2/Gondik Law Late Model Series WISSOTA Late Model: KME Late Model Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 6th | - | 12th (DNF) | - |
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| 8/12/2023 | Hibbing Raceway - Hibbing, MN Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 5th | - | - | 12th (DNF) |
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| 8/13/2023 | Proctor Speedway - Proctor, MN Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, Open Dirt Karts, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet, Flat Jr. 2 Clone Heavy | Results | | Charles Olson (WISSOTA Late Model) | 2nd | - | - | 5th |
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| 8/19/2023 | Ogilvie Raceway - Ogilvie, MN Kids Night - Meet the Drivers WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 3rd | - | - | 9th |
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| 8/26/2023 | Ogilvie Raceway - Ogilvie, MN Track Championship, HopeKids Night featuring The Structural Buildings Wissota Late Models WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 3rd | - | - | 20th (DNF) |
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| 8/31/2023 | Proctor Speedway - Proctor, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series A Modifieds, WISSOTA Modifieds | Results | | Charles Olson (WISSOTA Late Model) | 9th | - | 9th | - |
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