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| 5/5/2019 | Eagle Valley Speedway - Jim Falls, WI 2019 River Country Coop Season Opener Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 7th | - | - | 11th |
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| 5/17/2019 | Red Cedar Speedway - Menomonie, WI Midwest Mod Bonus Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 7th | - | - | 20th |
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| 5/26/2019 | Eagle Valley Speedway - Jim Falls, WI Haas, Inc. Memorial Day Madness w/ UMSS Sprint Cars - Night 1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Winged Sprints, Non-Winged Sprints, Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 8th | - | - | 20th |
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| 5/31/2019 | Red Cedar Speedway - Menomonie, WI Super Stock Bonus Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 7th | - | - | 16th |
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| 6/2/2019 | Eagle Valley Speedway - Jim Falls, WI Sunday Night WISSOTA Auto Racing Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 5th | - | - | 17th |
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| 6/7/2019 | Red Cedar Speedway - Menomonie, WI Street Stock Bonus Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 7th | - | - | 14th |
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| 6/8/2019 | Eagle Valley Speedway - Jim Falls, WI Chippewa Heavy Haul / Kirkpatrick Law Office Saturday Night WISSOTA Auto Racing Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 7th | - | - | 19th (DNF) |
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| 6/9/2019 | Eagle Valley Speedway - Jim Falls, WI Sunday Night WISSOTA Auto Racing w/ Northern Vintage Stock Cars Vintage Modifieds: Northern Vintage Stockcar Racers Stock Cars, Vintage Full Body Stock Cars, Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 6th (DNF) | - | - | 11th (DNF) |
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| 6/16/2019 | Eagle Valley Speedway - Jim Falls, WI Southworth Chevrolet / Tim's Automotive Machine Midwest Modified Special Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 8th (DNF) | - | - | 18th |
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| 6/21/2019 | Red Cedar Speedway - Menomonie, WI Race Of Champion Qualifier Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 8th | - | - | 25th |
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| 7/7/2019 | Eagle Valley Speedway - Jim Falls, WI Credit King Auto Sales Independence Day Bash - Dirt Kings Late Model Series - Fireworks Special Dirt Late Models: Dirt Kings Late Model Tour Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 8th | - | - | 15th (DNF) |
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| 7/12/2019 | Red Cedar Speedway - Menomonie, WI Military Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 8th | - | - | 19th |
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| 7/14/2019 | Red Cedar Speedway - Menomonie, WI Rumble At The Red Cedar World Of Outlaw Late Models Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Midwest Mods | Results | | Jason Olson (WISSOTA Midwest Mods) | 6th | - | - | 17th |
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| 7/26/2019 | Red Cedar Speedway - Menomonie, WI Dunn County Fair Night #2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 7th | - | - | 18th |
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| 8/9/2019 | Red Cedar Speedway - Menomonie, WI Regular Race Night/ROC Raindate Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 7th | - | - | 17th |
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| 8/11/2019 | Eagle Valley Speedway - Jim Falls, WI 3rd Annual K-Runk Memorial ($1,223 to-win MWM) River Country Coop American Heros Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 8th | - | 3rd | - |
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| 8/18/2019 | Eagle Valley Speedway - Jim Falls, WI Krug Towing Lonnie Leu Memorial presented by Lisa Leu & Iverson Trucking 30 MWM ($1,000 to win) Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 9th | - | - | 11th |
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| 8/23/2019 | Red Cedar Speedway - Menomonie, WI Hornets Bonus Night Vintage Modifieds: Northern Vintage Stockcar Racers Vintage Full Body Stock Cars, Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 6th | - | - | 23rd (DNF) |
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| 9/20/2019 | Red Cedar Speedway - Menomonie, WI 40th Annual Punky Manor Challenge Of Champions Heat Races DIRTcar UMP Modifieds, A Modifieds, B Modifieds, Dirt Late Models, Super Stocks, WISSOTA Modifieds | Results | | Jason Olson (B Modifieds) | 8th (DNF) | - | - | - |
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| 9/21/2019 | Red Cedar Speedway - Menomonie, WI 40th Annual Punky Manor Challenge Of Champions Night #3 Features DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Jason Olson (WISSOTA Midwest Mods) | 8th (DNF) | - | 7th | - |
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