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| 5/4/2019 | Rice Lake Speedway - Rice Lake, WI Regular 5 class program 67th Season Opener Best appearing car judging DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 3rd | - | - | 9th |
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| 5/10/2019 | Red Cedar Speedway - Menomonie, WI Modified Bonus Night Dirt Super Late Models, Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 5th | - | - | 8th |
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| 5/11/2019 | Rice Lake Speedway - Rice Lake, WI Trackside Collectibles 40, WISSOTA Late Models $2,000-To-Win DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 4th | - | - | 3rd |
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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 | | Eric Olson (WISSOTA Super Stock) | 5th | - | - | 6th |
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| 5/25/2019 | Rice Lake Speedway - Rice Lake, WI Sprint Car Night Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 1st | - | - | 16th (DNF) |
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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 | | Eric Olson (WISSOTA Super Stock) | 4th | - | - | 6th |
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| 6/1/2019 | Rice Lake Speedway - Rice Lake, WI Regular 5 Class Program DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 1st | - | - | 5th |
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| 6/15/2019 | Rice Lake Speedway - Rice Lake, WI Kid's Night & Bike Giveaways DIRTcar UMP Modifieds, 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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| 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 | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 5th |
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| 6/22/2019 | Rice Lake Speedway - Rice Lake, WI Advantage RV Modified Series, Schedule Change 5 class program DIRTcar UMP Modifieds, 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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| 6/29/2019 | Rice Lake Speedway - Rice Lake, WI Regular 5 class program DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 1st | - | - | 10th |
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| 7/3/2019 | Rice Lake Speedway - Rice Lake, WI Firecracker Special DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 3rd | - | - | 9th |
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| 7/9/2019 | ABC Raceway - Ashland, WI Red's Auto Badgerland 50 World of Outlaws Craftsman Late Model Series Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models, Dirt 6-cyl Stock Cars, WISSOTA Midwest Mods, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 16th (DNF) |
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| 7/13/2019 | Ogilvie Raceway - Ogilvie, MN World Of Outlaw Late Models & Fastlane Super Stock Special Dirt Super Late Models: World of Outlaws - Late Models WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series | Results | | Eric Olson (WISSOTA Super Stock) | 7th | - | 3rd | 14th |
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| 7/14/2019 | Granite City Motor Park - Sauk Rapids, MN Super Stock Special WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Hornet | Results | | Eric Olson (WISSOTA Super Stock) | 5th | - | - | 13th |
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| 7/20/2019 | ABC Raceway - Ashland, WI Fast Lane Motor Sports Superstock Series WISSOTA Super Stock: Fast Lane Motorsports Northland Super Stock Series Dirt 6-cyl Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock | Results | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 12th |
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| 7/25/2019 | Red Cedar Speedway - Menomonie, WI Dunn County Fair Night #1 Dirt Super Late Models, Hornets, WISSOTA Late Model, WISSOTA Street Stock | Results | | Eric Olson (WISSOTA Street Stock) | 2nd | - | - | 4th |
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| 7/27/2019 | Rice Lake Speedway - Rice Lake, WI Wollak Construction WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Street Stock) | 2nd | - | - | 10th | | Eric Olson (WISSOTA Super Stock) | 3rd | - | - | 3rd |
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| 7/30/2019 | Rice Lake Speedway - Rice Lake, WI 25th Annual Street Stock Little Dream WISSOTA Street Stock | Results | | Eric Olson (WISSOTA Street Stock) | 8th (DNF) | - | 3rd | 21st (DNF) |
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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 | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 8th |
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| 8/10/2019 | Rice Lake Speedway - Rice Lake, WI Hall of Fame Night, Rain Date for Race of Champions Qualifiers DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 7th |
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| 8/16/2019 | Red Cedar Speedway - Menomonie, WI 3rd Annual Mahder 55 Wissota Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series Dirt Super Late Models, WISSOTA Modifieds, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 5th | - | - | 6th |
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| 8/17/2019 | Rice Lake Speedway - Rice Lake, WI Bike Races DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 2nd | - | - | 12th (DNF) |
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| 8/24/2019 | Rice Lake Speedway - Rice Lake, WI Season Championships DIRTcar UMP Modifieds, 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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| 8/31/2019 | Rice Lake Speedway - Rice Lake, WI Labor Day Weekend Special DIRTcar UMP Modifieds, Hornets, 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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| 9/6/2019 | Gondik Law Speedway - Superior, WI Northern Nationals 410 Sprints - Winged: IRA Interstate Racing Association WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 3rd | - | - | DNS |
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| 9/13/2019 | Cedar Lake Speedway - New Richmond, WI Legendary 100 night 2 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks | Results | | Eric Olson (Super Stocks) | 3rd | - | - | - |
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| 9/14/2019 | Cedar Lake Speedway - New Richmond, WI Legendary 100 night 3 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks | Results | | Eric Olson (Super Stocks) | - | - | - | 8th |
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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 | | Eric Olson (Super Stocks) | 5th | - | - | - |
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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 | | Eric Olson (WISSOTA Super Stock) | 5th | - | - | 21st (DNF) |
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| 9/27/2019 | ABC Raceway - Ashland, WI 44th Annual Red Clay Classic presented by Tim's Automotive and Fastlane Motor Sports DIRTcar UMP Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Eric Olson (WISSOTA Super Stock) | 5th | - | 2nd | 7th |
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