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| 4/28/2023 | Gravity Park Speedway - Chilton, WI Races on the Speedway DIRTcar Sport Compact, Stock Cars, A Modifieds, B Modifieds, Street Stocks, Super Stocks | Results | | Taylor Olson (A Modifieds) | 5th | - | - | 15th |
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| 5/12/2023 | Eagle Valley Speedway - Jim Falls, WI Union Trailer & Power Equipment,River County Coop, Hope for Heather, Parsons Trophy Tour Night A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Modifieds, USRA Late Models, WISSOTA Pure Stock | Results | | Taylor Olson (A Modifieds) | 5th | - | - | 13th |
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| 5/13/2023 | Rice Lake Speedway - Rice Lake, WI WISSOTA Late Models Trackside Collectables 40 Plus 5 Class Program + "Best Appearing Judging" DIRTcar UMP Modifieds, Open Dirt Karts, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, Flat Jr. 2 Clone Heavy | Results | | Taylor Olson (WISSOTA Modifieds) | 8th (DNF) | - | 8th | - |
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| 5/19/2023 | Eagle Valley Speedway - Jim Falls, WI Gary Blaeser Memorial, West Hill Bar & Grill Night A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Modifieds, USRA Late Models, WISSOTA Pure Stock | Results | | Taylor Olson (A Modifieds) | 4th | - | - | 8th |
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| 5/20/2023 | Rice Lake Speedway - Rice Lake, WI Regular Racing 5 Class Program Best Appearing Car Awards DIRTcar UMP Modifieds, Open Dirt Karts, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, Flat Jr. 2 Clone Heavy | Results | | Taylor Olson (WISSOTA Modifieds) | 7th | - | - | 11th |
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| 5/26/2023 | Eagle Valley Speedway - Jim Falls, WI UMSS Sprint Car Special Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Modifieds, WISSOTA Pure Stock | Results | | Taylor Olson (A Modifieds) | 7th | - | - | 13th (DNF) |
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| 6/3/2023 | Cedar Lake Speedway - New Richmond, WI CLS Dash Race #5 A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, USRA Late Models, WISSOTA Super Stock | Results | | Taylor Olson (A Modifieds) | 7th | - | - | 17th |
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| 6/9/2023 | Eagle Valley Speedway - Jim Falls, WI 9th Annual Southworth Chevy & Tim's Automotive MWM Special A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Modifieds, USRA Late Models, WISSOTA Pure Stock | Results | | Taylor Olson (A Modifieds) | 6th | - | - | 12th |
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| 6/30/2023 | Eagle Valley Speedway - Jim Falls, WI Roland Machinery Christmas in July Night - Parsons Trophy Tour w/ Fireworks A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Modifieds, USRA Late Models, WISSOTA Pure Stock | Results | | Taylor Olson (A Modifieds) | 6th | - | - | 3rd |
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| 7/1/2023 | Madison Speedway - Madison, MN Race Night Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Taylor Olson (WISSOTA Modifieds) | 3rd | - | - | 5th |
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| 7/7/2023 | Eagle Valley Speedway - Jim Falls, WI Vintage Modifieds: Northern Vintage Stockcar Racers A Modifieds, B Modifieds, Street Stocks, Vintage Full Body Stock Cars, Hornets, Super Stocks, USRA Late Models, WISSOTA Pure Stock | Results | | Taylor Olson (A Modifieds) | 5th | - | - | 9th |
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| 7/14/2023 | Eagle Valley Speedway - Jim Falls, WI Kyle Runkle Memorial - Friday Night Racing Action A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Late Models, WISSOTA Pure Stock | Rain Out |
| 7/14/2023 | Red Cedar Speedway - Menomonie, WI Military Night * All Military get in free w Military ID to GrandstandsKids Night By Cardinal FG, SSR DIRTcar UMP Modifieds, Hornets, Open Dirt Karts, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, Flat Jr. 2 Clone Heavy | Results | | Taylor Olson (WISSOTA Modifieds) | 8th | - | - | 20th |
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| 7/15/2023 | ABC Raceway - Ashland, WI Hall of Fame Night presented by Zar's Bar Dirt 6-cyl Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Modifieds) | 7th | - | - | 13th |
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| 7/21/2023 | Eagle Valley Speedway - Jim Falls, WI Dalbeck Sales, Union Trailer, Stai Farms, Quality Propane, Spring Brook Express & Northwoods Lumber DIRTcar UMP Modifieds, A Modifieds, B Modifieds, Street Stocks, Super Stocks, USRA Modifieds, USRA Late Models, WISSOTA Pure Stock | Results | | Taylor Olson (A Modifieds) | 6th | - | - | DNS |
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| 8/5/2023 | ABC Raceway - Ashland, WI Small Car Classic presented by the ABC Sportsmen's Club and Heartland Communications Open Dirt Karts, Dirt 6-cyl Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock, Flat Jr. 2 Clone Heavy | Results | | Taylor Olson (WISSOTA Modifieds) | 6th (DNF) | - | - | DNS |
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| 8/18/2023 | Eagle Valley Speedway - Jim Falls, WI 22nd Annual Krug Towing & Chuck's Ripp's Bar & Grill Lonnie Leu Memorial A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Modifieds, USRA Late Models, WISSOTA Pure Stock | Results | | Taylor Olson (A Modifieds) | 4th | - | - | 9th |
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| 8/25/2023 | Eagle Valley Speedway - Jim Falls, WI Baxter Engines/Baxter's Speed Shop - Season Championships A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Late Models, WISSOTA Pure Stock | Results | | Taylor Olson (A Modifieds) | 4th | - | - | 10th |
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| 9/2/2023 | Rice Lake Speedway - Rice Lake, WI 5 Class Program WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Modifieds) | 6th | - | - | 13th (DNF) |
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| 9/8/2023 | Eagle Valley Speedway - Jim Falls, WI Jim Town Showdown - Parsons Trophy Tour A Modifieds, B Modifieds, Street Stocks, Hornets, Super Stocks, USRA Modifieds, USRA Late Models, WISSOTA Pure Stock | Results | | Taylor Olson (A Modifieds) | 3rd | - | - | 15th (DNF) |
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| 9/29/2023 | ABC Raceway - Ashland, WI Red Clay Classic B Modifieds, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Taylor Olson (WISSOTA Modifieds) | 10th | - | 8th | - |
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