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| 4/3/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #1 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Taylor Olson (Midwest Modifieds) | 7th | - | 6th | - |
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| 4/16/2021 | Cedar Lake Speedway - New Richmond, WI Legendary Opener Day 2 Limited Sprints - Winged: UMSS Winged 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 | | Taylor Olson (Midwest Modifieds) | - | - | - | 20th |
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| 4/23/2021 | Sk Speedway - Unity, WI Pure Stock Special with Regular Race Program Hornets, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 2nd | - | - | 4th |
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| 4/30/2021 | Sk Speedway - Unity, WI Kim Parson's Memorial Trophy Tour and Super Stock Special Hornets, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 7th | - | - | 8th |
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| 5/7/2021 | Eagle Valley Speedway - Jim Falls, WI UMSS Sprint Car Showdown Limited Sprints - Winged: UMSS Winged Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series 360 Sprints - Winged, A Modifieds, B Modifieds, Street Stocks, Winged Outlaw, Hornets, Super Stocks, Pure Stock, USRA Late Models | Results | | Taylor Olson (B Modifieds) | 5th | - | - | 13th |
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| 5/14/2021 | Sk Speedway - Unity, WI Regular Race Program with Spectator Racing Hornets, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 5th | - | - | 7th |
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| 5/28/2021 | Sk Speedway - Unity, WI Mid-West Modified Special with Regular Race Program Hornets, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 5th | - | - | 11th |
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| 6/4/2021 | Sk Speedway - Unity, WI Hornet Special with Regular Race Program Hornets, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | - | - | - | 4th |
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| 6/12/2021 | Tomahawk Speedway - Tomahawk, WI Pure Stock Da$h for Ca$h Stock Cars, Winged A-Class, B Modifieds, Street Stocks, Kid Karts Dirt, Pure Stock, IMCA Stock Car | Results | | Taylor Olson (B Modifieds) | - | - | - | - |
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| 6/18/2021 | Sk Speedway - Unity, WI Junk Yard Warriors with Regular Race Program Hornets, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 6th | - | - | 5th |
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| 6/25/2021 | Sk Speedway - Unity, WI Armed Forces Night with Regular Race Program Hornets, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 5th | - | - | 4th |
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| 7/2/2021 | Sk Speedway - Unity, WI Kids Night and Fireworks with Regular Race Program Hornets, Dirt 4 cyl Modifieds, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 1st | - | - | 5th (DNF) |
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| 7/9/2021 | Sk Speedway - Unity, WI K-9 Night with Regular Race Program Hornets, Dirt 4 cyl Modifieds, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 4th | - | - | 2nd |
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| 7/16/2021 | Eagle Valley Speedway - Jim Falls, WI Dalbeck Sales Modified Special Night 2 Vintage Modifieds: Northern Vintage Stockcar Racers A Modifieds, B Modifieds, Street Stocks, Vintage Full Body Stock Cars, Hornets, Super Stocks, Pure Stock | Results | | Taylor Olson (B Modifieds) | 6th | - | - | 11th |
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| 7/23/2021 | Eagle Valley Speedway - Jim Falls, WI Kyle Runkle Memorial A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, Pure Stock | Results | | Taylor Olson (B Modifieds) | 6th | - | - | 18th (DNF) |
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| 8/6/2021 | Sk Speedway - Unity, WI Kim Parson's Memorial Trophy Tour with Street Stock Special and Vintage Mods Hornets, Dirt 4 cyl Modifieds, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 5th | - | - | 5th |
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| 8/13/2021 | Sk Speedway - Unity, WI Powder Puff Race with Regular Race Program Hornets, Dirt 4 cyl Modifieds, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 2nd | - | - | 3rd |
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| 8/20/2021 | Sk Speedway - Unity, WI Season Championship with Mechanics Race Hornets, Dirt 4 cyl Modifieds, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Midwest Mods) | 5th (DNF) | - | - | 4th |
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| 9/10/2021 | Eagle Valley Speedway - Jim Falls, WI 2nd Annual - Dalbeck Logging - Union Trailer & Power Equipment Jim Town Showdown A Modifieds, B Modifieds, Street Stocks, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Modifieds | Results | | Taylor Olson (B Modifieds) | 6th | - | 2nd | 22nd |
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| 10/8/2021 | Sk Speedway - Unity, WI SK Clash Stock Cars, A Modifieds, B Modifieds, Street Stocks, Hornets, Dirt 4 cyl Modifieds, Super Stocks, Pure Stock | Results | | Taylor Olson (B Modifieds) | 9th | - | - | 11th |
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| 10/9/2021 | Sk Speedway - Unity, WI SK Clash Night 2 Stock Cars, A Modifieds, B Modifieds, Street Stocks, Hornets, Dirt 4 cyl Modifieds, Super Stocks, Pure Stock | Results | | Taylor Olson (B Modifieds) | 6th | - | - | 13th |
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