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| 6/15/2019 | Hibbing Raceway - Hibbing, MN Fortune Bay Resort Casino Night plus Kids Box Car Races Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Skylar Olson (WISSOTA Pure Stock) | 5th | - | - | 12th (DNF) |
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| 6/22/2019 | Hibbing Raceway - Hibbing, MN Rene Hughes Memorial 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 Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Skylar Olson (WISSOTA Pure Stock) | 5th | - | - | 11th |
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| 7/13/2019 | ABC Raceway - Ashland, WI Kid's Bike Race Night presented by Chicago Iron & Supplies Dirt 6-cyl Stock Cars, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Hornet | Results | | Skylar Olson (WISSOTA Pure Stock) | 8th | - | - | DNS |
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| 7/20/2019 | Hibbing Raceway - Hibbing, MN Chisholm City Merchants Night plus Power Wheels Races Vintage Modifieds, Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Skylar Olson (WISSOTA Pure Stock) | 6th | - | - | 11th (DNF) |
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| 7/27/2019 | Hibbing Raceway - Hibbing, MN Radko Iron and Supply Night plus Meet the Drivers!!!!! Vintage Modifieds, Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Skylar Olson (WISSOTA Pure Stock) | 8th | - | - | 18th (DNF) |
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