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| 3/10/2021 | Humboldt Speedway - Humboldt, KS Battle at the Bullring Practice Dirt Super Late Models, Factory Stocks, Stock Cars, A Modifieds, Midwest Modifieds, B Modifieds, Sport Compact, USRA B-Mods, USRA Modifieds | Rain Out |
| 4/16/2021 | Cedar Lake Speedway - New Richmond, WI Legendary Opener Day 2 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models | Results | | Cole Boston (Midwest Modifieds) | - | - | - | - |
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| 4/17/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 2nd | - | - | 21st (DNF) |
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| 5/1/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 4th | - | - | 14th |
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| 5/8/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with Mother's Day Special WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 4th | - | - | 18th |
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| 5/14/2021 | Gondik Law Speedway - Superior, WI Rescheduled 60th Season Opener WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 4th | - | - | 15th |
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| 5/15/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout - Armed Forces Night WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 4th | - | - | 12th |
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| 5/29/2021 | Ogilvie Raceway - Ogilvie, MN MN Modified Nationals presented by FYE Motorsports WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 8th | - | 7th | 21st |
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| 5/30/2021 | Ogilvie Raceway - Ogilvie, MN MN Modified Nationals presented by FYE Motorsports WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 6th | - | - | 14th |
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| 6/12/2021 | ABC Raceway - Ashland, WI RV Mod Series Presented by NAPA Auto of Ashland & Washburn A Modifieds, Dirt 6-cyl Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 5th | - | - | 17th |
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| 6/13/2021 | Proctor Speedway - Proctor, MN King on the Hill Modified Special WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 5th | - | - | 18th (DNF) |
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| 6/26/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 3rd | - | - | 14th |
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| 7/2/2021 | Gondik Law Speedway - Superior, WI 5th Annual Great Lakes Border Battle-Night #1 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 4th | - | - | 16th |
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| 7/3/2021 | Gondik Law Speedway - Superior, WI 5th Annual Great Lakes Border Battle-Night #2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 3rd | - | - | 8th |
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| 7/10/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with Fireworks Spectacular & Street Stock Special WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 6th | - | - | 11th |
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| 7/16/2021 | Ogilvie Raceway - Ogilvie, MN Inaugural USMTS Mod Wars A Modifieds: USMTS - United States Modified Touring Series WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 3rd | - | - | 22nd (DNF) |
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| 7/17/2021 | Ogilvie Raceway - Ogilvie, MN Inaugural USMTS Mod Wars A Modifieds: USMTS - United States Modified Touring Series WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 1st | - | - | 9th |
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| 7/24/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with FastLane Motorsports Northland Super Stock Seri WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 4th | - | - | 14th (DNF) |
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| 8/13/2021 | I-94 Speedway - Fergus Falls, MN Advantage RV Modified Tour Presented by Watertown Ford and Chrysler A Modifieds, Hornets, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock | Results | | Cole Boston (WISSOTA Midwest Mods) | 1st | - | - | 5th |
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| 8/14/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout/ ROC race to qualify for the W100 WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 2nd | - | - | 4th |
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| 8/15/2021 | Granite City Motor Park - Sauk Rapids, MN Regular Night Races also will be the ROC qualifier race for the WISSOTA 100 WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 3rd | - | - | 9th |
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| 8/21/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 4th | - | - | 21st (DNF) |
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| 9/9/2021 | Gondik Law Speedway - Superior, WI Northern Nationals-Night #1 305 Sprints - Non-Winged, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Cole Boston (WISSOTA Midwest Mods) | 5th | - | 1st | 14th |
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| 9/10/2021 | Gondik Law Speedway - Superior, WI Northern Nationals-Night #2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Cole Boston (WISSOTA Midwest Mods) | 9th (DNF) | - | 4th | 18th |
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| 9/11/2021 | Gondik Law Speedway - Superior, WI Northern Nationals-Night #3 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Cole Boston (WISSOTA Midwest Mods) | 3rd | - | - | 12th |
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| 9/16/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Midwest Mods | Results | | Cole Boston (Midwest Modifieds) | - | - | - | - |
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| 9/17/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 2 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Midwest Mods | Results | | Cole Boston (Midwest Modifieds) | - | - | - | - |
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| 9/18/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 3 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Midwest Mods | Results | | Cole Boston (Midwest Modifieds) | - | - | 3rd | 23rd |
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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 | | Cole Boston (WISSOTA Midwest Mods) | 3rd | - | - | - |
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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 | | Cole Boston (WISSOTA Midwest Mods) | - | - | 6th | - |
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