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| 6/1/2019 | Greenbush Race Park - Greenbush, MN GRP Racing Series Lightning Sprints, 600cc Modifieds, Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock | Results | | Dane Olson (600cc Modifieds) | 5th | - | - | 10th |
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| 6/19/2019 | Stuart Speedway - Stuart, IA Weekly Racing Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Street Stocks, 600cc Modifieds, Limited Sport Mod, Sport Compact | Results | | Dane Olson (600cc Modifieds) | 7th (DNF) | - | - | 14th (DNF) |
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| 6/20/2019 | Kossuth County Speedway - Algona, IA Micro Mods Hobby Stocks, A Modifieds, B Modifieds, Street Stocks, 600cc Modifieds, Enduro, Sport Compact | Results | | Dane Olson (600cc Modifieds) | 7th | - | - | 8th |
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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 | | Dane Olson (Winged Outlaw) | 5th | - | - | 8th |
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| 7/20/2019 | Greenbush Race Park - Greenbush, MN Lightning Sprint Special - Badger JC’s - Badger Lightning Sprints, 600cc Modifieds, Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock | Results | | Dane Olson (600cc Modifieds) | 5th | - | - | 9th |
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| 8/24/2019 | Emo Speedway - Emo, ON Fan Appreciation NIght Street Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds | Results | | Dane Olson (WISSOTA Midwest Mods) | 5th | - | - | 6th |
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| 8/31/2019 | Greenbush Race Park - Greenbush, MN Labor Day Special 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series B Modifieds, 305 Sprints - Non-Winged, Lightning Sprints, 600cc Modifieds, Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock | Results | | Dane Olson (600cc Modifieds) | 5th | - | - | 9th |
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| 9/1/2019 | Greenbush Race Park - Greenbush, MN Labor Day Special 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series B Modifieds, 305 Sprints - Non-Winged, Lightning Sprints, 600cc Modifieds, Sport Compact, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock | Results | | Dane Olson (600cc Modifieds) | 2nd | - | - | 4th |
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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 | | Dane Olson (Winged Outlaw) | 3rd | - | - | 16th (DNF) |
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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 | | Dane Olson (Winged Outlaw) | DNS | - | - | DNS |
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