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| 3/20/2019 | Humboldt Speedway - Humboldt, KS King of America Practice A Modifieds: USMTS - United States Modified Touring Series B Modifieds | Results | | Cole Boston (B Modifieds) | - | - | - | - |
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| 3/21/2019 | Humboldt Speedway - Humboldt, KS King of America-Battle@theBullring A Modifieds: USMTS - United States Modified Touring Series USRA Stock Cars: USRA Ironman B Modifieds, USRA B-Mods | Results | | Cole Boston (B Modifieds) | 9th | - | - | - |
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| 3/22/2019 | Humboldt Speedway - Humboldt, KS King of America-Battle@theBullring A Modifieds: USMTS - United States Modified Touring Series USRA Stock Cars: USRA Ironman B Modifieds, USRA B-Mods | Results | | Cole Boston (B Modifieds) | 8th | - | - | - |
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| 3/23/2019 | Humboldt Speedway - Humboldt, KS King of America-Battle@theBullring A Modifieds: USMTS - United States Modified Touring Series USRA Stock Cars: USRA Ironman B Modifieds, USRA B-Mods | Results | | Cole Boston (B Modifieds) | - | - | - | - |
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| 4/26/2019 | Ogilvie Raceway - Ogilvie, MN 11th Annual Season Opener Double Header Dirt 4 cyl Modifieds, Super Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 9th | - | 6th | - |
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| 5/4/2019 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout - with Hornet Spotlight WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 7th | - | 7th | - |
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| 5/11/2019 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout - Mother's Day Special with Mod Four Spotlight WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Rain Out |
| 5/25/2019 | Ogilvie Raceway - Ogilvie, MN Wehr Machine & Racing Products Minnesota Modified Nationals (FYE) WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | DNS | - | DNS | - |
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| 5/26/2019 | Ogilvie Raceway - Ogilvie, MN Wehrs Machine & Racing Products Minnesota Modified Nationals (FYE) WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 8th | - | 15th (DNF) | - |
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| 6/1/2019 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #5 A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Cole Boston (Midwest Modifieds) | 3rd | - | - | 15th |
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| 6/22/2019 | Ogilvie Raceway - Ogilvie, MN Midwest Power Series Sprint Car Special 360 Sprints - Winged: Midwest Power Series 360 Sprints - Non-Winged: MBTS Non-Wing Sprints WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 7th | - | - | 14th (DNF) |
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| 6/29/2019 | Gondik Law Speedway - Superior, WI 3rd Annual Great Lakes Border Battle-Night #1 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 8th (DNF) | - | 8th | - |
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| 6/30/2019 | Gondik Law Speedway - Superior, WI 3rd Annual Great Lakes Border Battle-Night #2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 6th | - | 13th (DNF) | - |
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| 7/6/2019 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout - Fireworks Spectacular WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 7th | - | 15th (DNF) | - |
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| 7/16/2019 | Ogilvie Raceway - Ogilvie, MN School Bus Race with Wissota Midwest Modified Special WISSOTA Midwest Mods | Results | | Cole Boston (WISSOTA Midwest Mods) | 11th | - | 11th | - |
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| 7/20/2019 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with Modified spotlight WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 8th (DNF) | - | - | 15th (DNF) |
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| 8/10/2019 | Ogilvie Raceway - Ogilvie, MN USMTS with Super Stock Spotlight A Modifieds: USMTS - United States Modified Touring Series Limited Sport Mod, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 5th | - | - | 16th |
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| 8/17/2019 | Ogilvie Raceway - Ogilvie, MN Season Championship WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 6th | - | - | 15th |
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| 8/18/2019 | Granite City Motor Park - Sauk Rapids, MN AFCO Race of Champions WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 5th | - | - | 15th |
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| 8/23/2019 | Ogilvie Raceway - Ogilvie, MN Harvest Cup Special with Wissota Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 7th | - | - | 17th |
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| 8/24/2019 | Ogilvie Raceway - Ogilvie, MN Harvest Cup Special with Wissota Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Super Stock | Results | | Cole Boston (WISSOTA Midwest Mods) | 6th | - | 5th | - |
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| 8/30/2019 | Grand Rapids Speedway - Grand Rapids, MN WISSOTA CLASSIC - WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Cole Boston (WISSOTA Midwest Mods) | 5th | - | - | 20th |
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| 8/31/2019 | Hibbing Raceway - Hibbing, MN Wollak Construction WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Cole Boston (WISSOTA Midwest Mods) | 6th | - | 11th (DNF) | - |
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| 9/1/2019 | Hibbing Raceway - Hibbing, MN Wollak Construction 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 | | Cole Boston (WISSOTA Midwest Mods) | 8th | - | 6th | - |
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| 9/13/2019 | Cedar Lake Speedway - New Richmond, WI Legendary 100 night 2 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks | Results | | Cole Boston (Midwest Modifieds) | 11th | - | - | - |
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| 9/14/2019 | Cedar Lake Speedway - New Richmond, WI Legendary 100 night 3 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks | Results | | Cole Boston (Midwest Modifieds) | - | - | 3rd | 24th (DNF) |
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| 10/4/2019 | Ogilvie Raceway - Ogilvie, MN MTH Fall Classic (FYE) Sport Compact, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Cole Boston (WISSOTA Midwest Mods) | 6th | - | 11th | - |
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