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| 6/1/2019 | Miller Central Speedway - Miller, SD Wollak Construction WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series A Modifieds, Super Stocks, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 5th | - | - | 7th |
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| 6/8/2019 | Miller Central Speedway - Miller, SD Reg Show- All Classes Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 3rd | - | - | 5th |
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| 6/22/2019 | Miller Central Speedway - Miller, SD Race of Champions Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 2nd | - | - | 6th |
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| 6/28/2019 | Black Hills Speedway - Rapid City, SD WISSOTA R.O.C & WISSOTA Street Stock Special $1,000 to win 305 Sprints - Winged, Hobby Stocks, A Modifieds, Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 5th | - | - | 6th |
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| 7/13/2019 | Miller Central Speedway - Miller, SD All Classes (Rain out date for ROC Race) Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 7th | - | - | 3rd |
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| 7/27/2019 | Miller Central Speedway - Miller, SD Tri-State Late Model Series Dirt Late Models: Tri-State Late Models A Modifieds, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 4th | - | - | 4th |
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| 8/3/2019 | Miller Central Speedway - Miller, SD Sponsored by Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 3rd | - | - | 8th |
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| 8/17/2019 | Miller Central Speedway - Miller, SD Season Championship Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Rain Out |
| 9/11/2019 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 - Day 1 Dirt 4 cyl Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 9th (DNF) | - | - | - |
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| 9/12/2019 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 - Day 2 Dirt 4 cyl Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | - | - | - | - |
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| 9/13/2019 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 - Day 3 WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 7th | - | - | 15th |
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| 9/14/2019 | I-94 Speedway - Fergus Falls, MN WISSOTA 100 FINALE! WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Phillips (WISSOTA Street Stock) | 11th (DNF) | - | - | - |
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