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| 5/25/2019 | Hibbing Raceway - Hibbing, MN Hibbing City Merchants Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Chris Olson (WISSOTA Late Model) | 2nd | - | - | 4th |
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| 6/1/2019 | Hibbing Raceway - Hibbing, MN Quad Cities Merchants Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Chris Olson (WISSOTA Late Model) | 1st | - | - | 8th |
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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 | | Chris Olson (WISSOTA Late Model) | 1st | - | - | 9th |
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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: 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 | | Chris Olson (WISSOTA Late Model) | 1st | - | - | 9th |
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| 7/11/2019 | Grand Rapids Speedway - Grand Rapids, MN 305 Sprints - Non-Winged, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Chris Olson (WISSOTA Late Model) | 2nd | - | - | 8th |
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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 | | Chris Olson (WISSOTA Late Model) | 7th | - | - | 17th (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 | | Chris Olson (WISSOTA Late Model) | 6th | - | - | 11th |
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| 8/1/2019 | Grand Rapids Speedway - Grand Rapids, MN WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Chris Olson (WISSOTA Late Model) | 1st | - | - | 13th (DNF) |
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| 8/10/2019 | Hibbing Raceway - Hibbing, MN Weekly Racing plus Hall of Fame Induction Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Chris Olson (WISSOTA Late Model) | 1st | - | - | 4th |
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| 8/15/2019 | Grand Rapids Speedway - Grand Rapids, MN WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Super Stock | Results | | Chris Olson (WISSOTA Late Model) | 5th | - | - | 10th |
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| 8/17/2019 | Hibbing Raceway - Hibbing, MN Bud Light Season Championship Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Chris Olson (WISSOTA Late Model) | 9th (DNF) | - | - | 13th |
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| 8/29/2019 | Proctor Speedway - Proctor, MN 47th Annual Silver 1000 WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Modifieds | Results | | Chris Olson (WISSOTA Late Model) | 7th | - | 2nd | 17th |
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| 8/30/2019 | Grand Rapids Speedway - Grand Rapids, MN WISSOTA CLASSIC - WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Chris Olson (WISSOTA Late Model) | 6th | - | - | 16th |
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| 8/31/2019 | Hibbing Raceway - Hibbing, MN Wollak Construction WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Super Stock | Results | | Chris Olson (WISSOTA Late Model) | 5th | - | 3rd | 26th |
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