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| 5/1/2021 | Rice Lake Speedway - Rice Lake, WI 69th Season Opener, 5 Class Program, Best Appearing Car Judging, Five Class Program WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Thomas O'Brien (WISSOTA Street Stock) | 6th (DNF) | - | - | 8th |
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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 | | Thomas O'Brien (WISSOTA Street Stock) | 7th | - | - | 8th |
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| 5/16/2021 | Granite City Motor Park - Sauk Rapids, MN Kid's Night - Bicycle Giveaway WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Thomas O'Brien (WISSOTA Street Stock) | 4th | - | - | 8th |
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| 5/22/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Thomas O'Brien (WISSOTA Street Stock) | 4th | - | - | 7th |
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| 5/29/2021 | Rice Lake Speedway - Rice Lake, WI Swant Graber presents Structural Buildings WISSOTA Challenge Series (No Mods) plus PS, St S, SS, MWM WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Thomas O'Brien (WISSOTA Street Stock) | 6th | - | - | 22nd (DNF) |
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| 6/12/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Thomas O'Brien (WISSOTA Street Stock) | 6th | - | - | 12th |
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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 | | Thomas O'Brien (WISSOTA Street Stock) | 8th | - | 7th | - |
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| 7/31/2021 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout and Bus Races WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Thomas O'Brien (WISSOTA Street Stock) | 5th | - | - | 10th (DNF) |
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| 8/3/2021 | Rice Lake Speedway - Rice Lake, WI S&R Towing Twenty Seventh Annual Street Stock Little Dream WISSOTA Street Stock | Results | | Thomas O'Brien (WISSOTA Street Stock) | 6th | - | 7th | - |
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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 | | Thomas O'Brien (WISSOTA Street Stock) | 4th | - | - | 7th |
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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 | | Thomas O'Brien (WISSOTA Street Stock) | 7th | - | - | - |
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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 | | Thomas O'Brien (WISSOTA Street Stock) | - | - | 6th | - |
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| 10/15/2021 | Gondik Law Speedway - Superior, WI Inaugural Can-Am Clash-Night #1 Fueled by Superior Fuel WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Thomas O'Brien (WISSOTA Street Stock) | 2nd | - | - | 10th |
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| 10/22/2021 | Ogilvie Raceway - Ogilvie, MN Topless Nationals Night One A Modifieds, B Modifieds, Street Stocks, Dirt 4 cyl Modifieds, Super Stocks | Results | | Thomas O'Brien (Street Stocks) | 7th | - | - | - |
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| 10/23/2021 | Ogilvie Raceway - Ogilvie, MN Topless Nationals Night Two A Modifieds, Winged A-Class, B Modifieds, Street Stocks, Dirt 4 cyl Modifieds, Super Stocks | Results | | Thomas O'Brien (Street Stocks) | - | - | - | 19th (DNF) |
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