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| 5/15/2020 | Cedar Lake Speedway - New Richmond, WI School Bus Race Night!! 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Midwest Modifieds, 305 Sprints - Non-Winged | Results | | Gavin Olson (Midwest Modifieds) | 7th | - | - | 18th |
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| 5/23/2020 | Cedar Lake Speedway - New Richmond, WI Pack The Track Night and Cook Memorial FREE GRANDSTAND ENTRY! Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Midwest Modifieds, Winged A-Class, Pony Stock, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 7th | - | 7th | - |
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| 5/30/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #5 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Modifieds | Results | | Gavin Olson (Midwest Modifieds) | 6th | - | 4th | - |
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| 6/6/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #6 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 5th | - | - | 17th |
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| 6/20/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #7 & Kids Night Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Super Stocks | Results | | Gavin Olson (Midwest Modifieds) | 5th | - | - | 17th |
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| 6/27/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #8 & Firecracker Special! 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series DIRTcar UMP Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 8th | - | 7th | - |
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| 7/11/2020 | Cedar Lake Speedway - New Richmond, WI NASCAAR Dash Race #9 DIRTcar UMP Modifieds, A Modifieds, Midwest Modifieds, Dirt Late Models, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 9th | - | 7th | - |
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| 7/21/2020 | Ogilvie Raceway - Ogilvie, MN School Bus Races with Street Stock Tour Special WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 7th | - | - | 15th |
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| 7/25/2020 | Ogilvie Raceway - Ogilvie, MN Saturday Night Shootout with Mod Four Spotlight USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Hornet | Results | | Gavin Olson (WISSOTA Midwest Mods) | 7th | - | - | 16th |
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| 8/1/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #12 A Modifieds, Midwest Modifieds, Super Stocks, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 10th | - | 16th | - |
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| 8/15/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #13 A Modifieds, Midwest Modifieds, 600cc Modifieds, Super Stocks, USRA Modifieds, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 7th | - | 3rd | - |
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| 8/22/2020 | Cedar Lake Speedway - New Richmond, WI NASCAR Dash Race #14 & Season Championship 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series DIRTcar UMP Modifieds, A Modifieds, Midwest Modifieds, Dirt Late Models, 305 Sprints - Non-Winged, Super Stocks, USRA Modifieds, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | 9th | - | 8th | - |
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| 8/28/2020 | Cedar Lake Speedway - New Richmond, WI 3rd Annual Traditional Sprint Car Challenge Day 1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series Vintage Modifieds: Northern Vintage Stockcar Racers Midwest Modifieds, 305 Sprints - Non-Winged, Vintage Full Body Stock Cars | Results | | Gavin Olson (Midwest Modifieds) | 8th | - | - | 14th |
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| 9/16/2020 | Cedar Lake Speedway - New Richmond, WI Open Practice : All Classes 6-9pm A Modifieds, Midwest Modifieds, Dirt Late Models, WISSOTA Midwest Mods | Results | | Gavin Olson (Midwest Modifieds) | - | - | - | - |
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| 9/17/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Gavin Olson (Midwest Modifieds) | - | - | - | - |
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| 9/18/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 2 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Gavin Olson (Midwest Modifieds) | - | - | - | - |
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| 9/19/2020 | Cedar Lake Speedway - New Richmond, WI 15th Annual Legendary 100 Day 3 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: UMSS - Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods | Results | | Gavin Olson (Midwest Modifieds) | - | - | DNS | - |
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