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| 4/3/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #1 360 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 | - | - | 19th |
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| 4/16/2021 | Cedar Lake Speedway - New Richmond, WI Legendary Opener Day 2 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | - | - | - | - |
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| 4/17/2021 | Cedar Lake Speedway - New Richmond, WI Legendary Open Day 3 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models | Results | | Gavin Olson (Midwest Modifieds) | - | - | - | - |
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| 5/1/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #4 360 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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| 5/14/2021 | Red Cedar Speedway - Menomonie, WI Regular Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 7th | - | - | 13th |
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| 5/15/2021 | Cedar Lake Speedway - New Richmond, WI School Bus Special 360 Sprints - Non-Winged: Traditional Sprint Car Series Midwest Modifieds, 305 Sprints - Non-Winged, Generic 1 | Results | | Gavin Olson (Midwest Modifieds) | 5th | - | - | 19th |
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| 5/22/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #5 360 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) | 9th | - | 7th | - |
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| 5/29/2021 | Deer Creek Speedway - Spring Valley, MN 18th Annual USMTS Southern MN Spring Challenge A Modifieds: USMTS - United States Modified Touring Series USRA B-Mods, USRA Stock Cars, WISSOTA Midwest Mods | Results | | Gavin Olson (WISSOTA Midwest Mods) | 3rd | - | - | 10th |
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| 6/5/2021 | Cedar Lake Speedway - New Richmond, WI CLS Dash #6 360 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) | 5th | - | - | 19th (DNF) |
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| 6/11/2021 | Red Cedar Speedway - Menomonie, WI Race of Champions Raindate - Regular Night Hornets, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 6th | - | - | 16th |
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| 6/12/2021 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 5th | - | - | 16th |
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| 6/19/2021 | 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 | | Gavin Olson (WISSOTA Midwest Mods) | 5th | - | - | 12th |
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| 7/3/2021 | Deer Creek Speedway - Spring Valley, MN Fireworks - Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 5th | - | - | 11th |
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| 7/10/2021 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 3rd | - | - | 14th (DNF) |
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| 7/17/2021 | Deer Creek Speedway - Spring Valley, MN Tasseldega Nights - Points Race - FREE Grandstands USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 1st | - | - | 14th (DNF) |
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| 7/24/2021 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, USRA Late Models, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 7th (DNF) | - | - | 11th |
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| 7/31/2021 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Rain Out |
| 8/14/2021 | Deer Creek Speedway - Spring Valley, MN Veterans Night- Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 3rd | - | - | 19th (DNF) |
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| 8/21/2021 | Deer Creek Speedway - Spring Valley, MN Points Race USRA B-Mods, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 6th | - | - | 14th |
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| 9/16/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 1 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Midwest Mods | Results | | Gavin Olson (Midwest Modifieds) | - | - | - | - |
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| 9/17/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 2 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Midwest Mods | Results | | Gavin Olson (Midwest Modifieds) | - | - | - | - |
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| 9/18/2021 | Cedar Lake Speedway - New Richmond, WI 16th Annual Legendary 100 Night 3 Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series A Modifieds, Midwest Modifieds, Street Stocks, Dirt Late Models, 305 Sprints - Non-Winged, Pony Stock, Super Stocks, Pure Stock, USRA Late Models, WISSOTA Midwest Mods | Results | | Gavin Olson (Midwest Modifieds) | - | - | 11th | - |
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| 9/24/2021 | Red Cedar Speedway - Menomonie, WI 41st Annual Punky Manor Challenge of Champions Night #1 Heats WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 8th | - | - | - |
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| 9/25/2021 | Red Cedar Speedway - Menomonie, WI 41st Annual Punky Manor Challenge Of Champions Features & Hall of Fame Induction WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Gavin Olson (WISSOTA Midwest Mods) | 8th | - | 9th | - |
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