| | Heat | Dash | B Feature | A Feature |
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| 5/17/2020 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Weekly Racing Dirt Late Models, USRA Modifieds, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | DNS | - | - | 17th (DNF) |
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| 6/7/2020 | Casino Speedway - Watertown, SD WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 7th | - | - | 16th (DNF) |
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| 6/14/2020 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Weekly Series Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 7th (DNF) | - | - | 14th (DNF) |
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| 6/28/2020 | Casino Speedway - Watertown, SD WISSOTA Marilyn Olson Late Model Special WISSOTA Late Model: Wissota Late Model Challenge Series Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Dean Small (WISSOTA Midwest Mods) | DNS | - | - | 20th (DNF) |
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| 7/12/2020 | Casino Speedway - Watertown, SD WISSOTA Weekly Dirt Track Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 6th (DNF) | - | - | DNS |
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| 7/18/2020 | Madison Speedway - Madison, MN Season Opener Stock Cars, Dirt Late Models, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dean Small (WISSOTA Midwest Mods) | 8th (DNF) | - | - | 24th (DNF) |
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| 7/25/2020 | Madison Speedway - Madison, MN Steffes Street Stock Tour Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dean Small (WISSOTA Midwest Mods) | 7th (DNF) | - | - | 19th (DNF) |
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