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| 5/1/2021 | Miller Central Speedway - Miller, SD Season Opener- Sponsored by Quoin Financial Bank Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 5th | - | - | 13th |
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| 5/15/2021 | Miller Central Speedway - Miller, SD Regular Races Sponsored by Agtegra Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 2nd | - | - | 13th (DNF) |
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| 5/22/2021 | Miller Central Speedway - Miller, SD Regular Races sponsored by Nelson's HB Seed Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 6th | - | - | 8th |
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| 6/3/2021 | Dakota State Fair Speedway - Huron, SD Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 5th | - | - | 21st (DNF) |
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| 6/12/2021 | Miller Central Speedway - Miller, SD Tri-State Late Model Series Dirt Late Models: Tri-State Late Models Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 6th | - | - | 6th |
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| 6/18/2021 | Black Hills Speedway - Rapid City, SD Dillon Heinzerling Midwest Mod Memorial Race IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 3rd | - | - | 11th (DNF) |
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| 7/2/2021 | Black Hills Speedway - Rapid City, SD FIREWORKS Special! 360 Sprint Cars, Wissota Street Stock, IMCA Hobby Stock, Wissota Mod 4 Specials 360 Sprints - Winged, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 4th | - | - | 15th |
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| 7/9/2021 | Black Hills Speedway - Rapid City, SD WISSOTA Midwest Mod Border Clash 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 1st | - | - | 6th |
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| 7/23/2021 | Black Hills Speedway - Rapid City, SD High Plains Late Model Tour 360 Sprints - Winged, Dirt Super Late Models, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 5th | - | - | 14th (DNF) |
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| 7/30/2021 | Black Hills Speedway - Rapid City, SD Regular Race 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 4th | - | - | 6th |
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| 8/13/2021 | Miller Central Speedway - Miller, SD Season Championship Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 3rd | - | - | 20th |
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| 8/14/2021 | Miller Central Speedway - Miller, SD Advantage RV Mod Tour A Modifieds, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 6th | - | - | 12th |
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| 8/21/2021 | Dakota State Fair Speedway - Huron, SD Stock Car Racing WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 2nd | - | - | 10th |
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