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| 5/1/2021 | North Central Speedway - Brainerd, MN Ron Johnson memorial race Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Charles Olson (A Modifieds) | 5th | - | - | 19th |
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| 5/8/2021 | North Central Speedway - Brainerd, MN Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Charles Olson (A Modifieds) | 1st | - | - | 3rd |
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| 5/15/2021 | North Central Speedway - Brainerd, MN Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Charles Olson (A Modifieds) | 1st | - | - | 2nd |
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| 5/22/2021 | North Central Speedway - Brainerd, MN Meet the drivers Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Charles Olson (A Modifieds) | 5th | - | - | 7th |
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| 5/29/2021 | North Central Speedway - Brainerd, MN Weekly racing Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Charles Olson (A Modifieds) | 5th | - | - | 15th |
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| 6/12/2021 | North Central Speedway - Brainerd, MN Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Charles Olson (A Modifieds) | 2nd | - | - | 8th |
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| 6/19/2021 | North Central Speedway - Brainerd, MN Hobby Stocks, A Modifieds, B Modifieds, Sport Compact, IMCA Stock Car, WISSOTA Mod Four, WISSOTA Super Stock | Results | | Charles Olson (A Modifieds) | 1st | - | - | 2nd |
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| 6/24/2021 | Princeton Speedway - Princeton, MN Siercks Memorial Hobby Stocks, A Modifieds, B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Charles Olson (IMCA Modified) | - | - | - | - |
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| 6/25/2021 | North Central Speedway - Brainerd, MN 10000 lakes 10k A Modifieds, B Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Charles Olson (IMCA Modified) | 3rd | - | 2nd | 22nd (DNF) |
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| 6/26/2021 | North Central Speedway - Brainerd, MN 10000 lakes 10k IMCA Modified: Land of Ten Thousand Lakes 10K A Modifieds, B Modifieds, IMCA Northern SportMod, IMCA Stock Car | Results | | Charles Olson (IMCA Modified) | 7th | - | 16th (DNF) | - |
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| 8/22/2021 | Proctor Speedway - Proctor, MN 70th Anniversary Season Championship WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 6th | - | - | 11th (DNF) |
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| 9/2/2021 | Proctor Speedway - Proctor, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Modifieds | Results | | Charles Olson (WISSOTA Late Model) | 8th | - | 3rd | 22nd (DNF) |
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| 9/4/2021 | Hibbing Raceway - Hibbing, MN Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 3rd | - | - | 13th |
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| 9/5/2021 | Hibbing Raceway - Hibbing, MN Structural Buildings WISSOTA Late Model Challenge Series - Championship Night WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 5th | - | - | 12th |
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| 9/24/2021 | Red Cedar Speedway - Menomonie, WI 41st Annual Punky Manor Challenge of Champions Night #1 Heats WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Charles Olson (WISSOTA Late Model) | 7th | - | - | - |
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| 9/25/2021 | Red Cedar Speedway - Menomonie, WI 41st Annual Punky Manor Challenge Of Champions Features & Hall of Fame Induction WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Charles Olson (WISSOTA Late Model) | 7th | - | 7th | - |
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| 10/8/2021 | Ogilvie Raceway - Ogilvie, MN Fall Classic presented by FYE Motorsports A Modifieds, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | 5th | - | - | - |
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| 10/9/2021 | Ogilvie Raceway - Ogilvie, MN Fall Classic presented by FYE Motorsports A Modifieds, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Charles Olson (WISSOTA Late Model) | - | - | 3rd | 13th |
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