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| 5/30/2020 | Rice Lake Speedway - Rice Lake, WI 68th Season Opener: Five Class program Best Appearing Car Judging WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 3rd |
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| 6/6/2020 | Rice Lake Speedway - Rice Lake, WI WISSOTA Late Models plus Supers, Streets, MWM, and Pures no Mods DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 7th (DNF) | - | - | 4th |
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| 6/12/2020 | Eagle Valley Speedway - Jim Falls, WI Friday Night WISSOTA Auto Racing Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 13th (DNF) |
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| 6/27/2020 | Rice Lake Speedway - Rice Lake, WI 5 Class program WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 3rd | - | - | 3rd |
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| 7/2/2020 | Rice Lake Speedway - Rice Lake, WI Fire Cracker Special, Barron County Relay at the Races, Five Classes WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 7th (DNF) | - | - | 5th |
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| 7/11/2020 | Rice Lake Speedway - Rice Lake, WI Five Class Program Plus Street Stock Bonus Night WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 1st | - | - | 4th |
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| 7/17/2020 | Eagle Valley Speedway - Jim Falls, WI Friday Night WISSOTA Auto Racing Hornets, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 6th | - | - | 6th |
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| 7/24/2020 | Eagle Valley Speedway - Jim Falls, WI Friday Night WISSOTA Auto Racing - 4th Annual Kyle Runkel Memorial Hornets, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 1st |
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| 7/31/2020 | Eagle Valley Speedway - Jim Falls, WI EDI Nordson, Don Hazelton Memorial Friday Night WISSOTA Auto Racingm with Northern Vintage Racing Hornets, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 4th | - | - | 3rd |
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| 8/4/2020 | Rice Lake Speedway - Rice Lake, WI 26th Annual Street Stock Little Dream Race-Rain Date August 5th WISSOTA Street Stock | Results | | Eric Olson (WISSOTA Street Stock) | 2nd | - | - | 24th (DNF) |
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| 8/14/2020 | Eagle Valley Speedway - Jim Falls, WI 19th Annual Lonnie Leu Memorial by Krug's Towing & Lisa Leu Hornets, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 5th | - | - | 7th |
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| 8/15/2020 | Rice Lake Speedway - Rice Lake, WI Hall of Fame Night - Five Class Program WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 5th |
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| 8/22/2020 | Rice Lake Speedway - Rice Lake, WI Bike Races - Five Class Program Plus Kid's Night WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 2nd |
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| 8/29/2020 | Rice Lake Speedway - Rice Lake, WI Season Fiinale Five Classes Draw redraw WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 1st | - | - | 2nd |
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| 9/3/2020 | ABC Raceway - Ashland, WI Prelude to the Clay USRA Modifieds, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 5th | - | - | 10th |
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| 9/5/2020 | Rice Lake Speedway - Rice Lake, WI Labor Day Special , Five Classes USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Street Stock) | 1st | - | - | 5th | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 5th |
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| 9/11/2020 | Cedar Lake Speedway - New Richmond, WI Sprints Weekend Limited Sprints - Winged: UMSS Winged Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Winged A-Class, Street Stocks, 305 Sprints - Non-Winged | Results | | Eric Olson (Street Stocks) | 3rd | - | - | 5th |
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| 9/17/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 1 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 Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Eric Olson (Street Stocks) | - | - | - | 4th | | Eric Olson (Super Stocks) | - | - | - | 6th |
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| 9/18/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 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 Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Eric Olson (Street Stocks) | - | - | - | 14th | | Eric Olson (Super Stocks) | - | - | - | - |
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| 9/19/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 3 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 Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Eric Olson (Street Stocks) | - | - | - | 4th | | Eric Olson (Super Stocks) | - | - | - | 21st |
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| 9/25/2020 | Eagle Valley Speedway - Jim Falls, WI Jim Town Showdown Hornets, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 8th (DNF) | - | - | 8th |
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| 10/2/2020 | ABC Raceway - Ashland, WI Red Clay Classic WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Canceled |