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| 4/20/2019 | Cedar Lake Speedway - New Richmond, WI CLS Dash / Tech Day 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 8th | - | 8th | - |
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| 5/4/2019 | Cedar Lake Speedway - New Richmond, WI 360 Sprints - Winged: Midwest Power Series A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 10th | - | - | 18th (DNF) |
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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 | | Gavin Olson (WISSOTA Midwest Mods) | 7th | - | 10th | - |
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| 5/25/2019 | Cedar Lake Speedway - New Richmond, WI PACK THE TRACK and Cook Memorial Night Midwest Modifieds, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 5th | - | - | 15th |
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| 6/1/2019 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #5 A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 7th | - | - | 10th |
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| 6/7/2019 | Red Cedar Speedway - Menomonie, WI Street Stock Bonus Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 4th | - | - | 13th |
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| 6/22/2019 | Cedar Lake Speedway - New Richmond, WI Dash Race #6: Eric Herbison Memorial and Kids Night A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks | Results | | Gavin Olson (Midwest Modifieds) | 8th | - | - | 26th |
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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 | | Gavin Olson (WISSOTA Midwest Mods) | 6th | - | - | 10th (DNF) |
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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 | | Gavin Olson (WISSOTA Midwest Mods) | 8th | - | - | 17th |
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| 7/12/2019 | Red Cedar Speedway - Menomonie, WI Military Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 7th | - | - | 21st |
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| 7/13/2019 | Cedar Lake Speedway - New Richmond, WI Dash Race #8: Late Models, Modifieds, Pro Stocks, Limited Late Models and Midwest Mods A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 8th | - | - | 12th |
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| 7/26/2019 | Red Cedar Speedway - Menomonie, WI Dunn County Fair Night #2 WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 8th | - | - | 17th |
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| 7/27/2019 | Cedar Lake Speedway - New Richmond, WI CLS Dash with Northern Renegades Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 7th | - | - | 14th |
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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 | | Gavin Olson (WISSOTA Midwest Mods) | 8th | - | - | 14th |
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| 8/17/2019 | Cedar Lake Speedway - New Richmond, WI CLS Dash 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 5th | - | - | 16th |
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| 8/23/2019 | Cedar Lake Speedway - New Richmond, WI Traditional North South Shoot Out Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series Midwest Modifieds, 305 Sprints - Non-Winged, Super Stocks | Results | | Gavin Olson (Midwest Modifieds) | 7th | - | - | 12th |
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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 | | Gavin Olson (WISSOTA Midwest Mods) | 6th | - | - | 13th |
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| 8/30/2019 | Red Cedar Speedway - Menomonie, WI Championship Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Pure Stock, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 7th | - | - | 20th |
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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 | | Gavin Olson (WISSOTA Midwest Mods) | 8th | - | - | 19th |
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| 9/13/2019 | Cedar Lake Speedway - New Richmond, WI Legendary 100 night 2 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks | Results | | Gavin Olson (Midwest Modifieds) | 15th | - | - | - |
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| 9/14/2019 | Cedar Lake Speedway - New Richmond, WI Legendary 100 night 3 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks | Results | | Gavin Olson (Midwest Modifieds) | - | 10th | 12th (DNF) | - |
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