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| 5/4/2019 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 6th | - | - | DNS |
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| 5/10/2019 | Chateau Speedway - Lansing, MN Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 7th | - | - | 12th |
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| 5/11/2019 | Deer Creek Speedway - Spring Valley, MN Points Race A Modifieds, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 7th (DNF) | - | - | 19th |
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| 5/24/2019 | Chateau Speedway - Lansing, MN Stock Cars, Sport Compact, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 9th | - | - | 11th |
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| 5/25/2019 | Deer Creek Speedway - Spring Valley, MN 17th Annual Southern MN Spring Challenge A Modifieds: USMTS - United States Modified Touring Series USRA Stock Cars: USRA Ironman USRA B-Mods, WISSOTA Midwest Mods | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 6th | - | 10th | - |
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| 5/26/2019 | Chateau Speedway - Lansing, MN Spirit of 83 Memorial Winged Outlaw, Pure Stock, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Hornet | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 6th (DNF) | - | - | DNS |
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| 6/14/2019 | Chateau Speedway - Lansing, MN USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 6th | - | - | 11th |
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| 6/21/2019 | Chateau Speedway - Lansing, MN Inaugural Chateau Hall Of Fame Induction Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 7th (DNF) | - | - | 10th |
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| 6/22/2019 | Deer Creek Speedway - Spring Valley, MN Pink Out Night - Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 6th | - | - | 25th |
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| 6/28/2019 | Chateau Speedway - Lansing, MN “The Dirt Show” Night Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 4th | - | - | 6th |
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| 6/29/2019 | Deer Creek Speedway - Spring Valley, MN Fireworks - Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 7th | - | - | DNS |
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| 8/2/2019 | Chateau Speedway - Lansing, MN Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 6th | - | - | 16th (DNF) |
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| 8/3/2019 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 7th | - | - | 17th |
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| 8/9/2019 | Chateau Speedway - Lansing, MN Pack The Stands $5 admission Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | DNS | - | - | 8th |
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| 8/10/2019 | Deer Creek Speedway - Spring Valley, MN WISSOTA ROC - Points Race A Modifieds, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 6th | - | - | DNS |
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| 9/27/2019 | Chateau Speedway - Lansing, MN Autumn Extravaganza Night 1 Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 6th | - | 7th | - |
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| 9/28/2019 | Chateau Speedway - Lansing, MN Autumn Extravaganza Night 2 Winged Outlaw, USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Hornet | Results | | Britt Olson Jr (WISSOTA Midwest Mods) | 6th | - | - | 16th |
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