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| 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 | | Mike Boston (A Modifieds) | - | - | - | 18th (DNF) |
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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 | | Mike Boston (WISSOTA Modifieds) | 6th | - | - | 19th |
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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 | | Mike Boston (WISSOTA Modifieds) | 6th | - | - | 12th |
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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 | | Mike Boston (WISSOTA Modifieds) | 8th | - | - | 18th |
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| 6/10/2021 | Grand Rapids Speedway - Grand Rapids, MN Advantage RV Mod Tour Non-Winged Sprints, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Mike Boston (WISSOTA Modifieds) | 5th | - | - | 21st (DNF) |
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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 | | Mike Boston (WISSOTA Modifieds) | 6th | - | 8th | - |
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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 | | Mike Boston (WISSOTA Modifieds) | 6th (DNF) | - | - | 18th (DNF) |
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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 | | Mike Boston (WISSOTA Modifieds) | 6th | - | - | 10th |
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