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| 5/26/2019 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Casino Speedway Memorial WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 6th | - | 6th | - |
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| 6/2/2019 | Casino Speedway - Watertown, SD Wollak Construction WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 8th | - | - | 20th (DNF) |
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| 6/16/2019 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Father's Day Races WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 9th | - | DNS | - |
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| 6/22/2019 | Madison Speedway - Madison, MN Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Rain Out |
| 6/29/2019 | Madison Speedway - Madison, MN Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dean Small (WISSOTA Midwest Mods) | 6th | - | - | 10th |
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| 6/30/2019 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Mid-Season Championships 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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| 7/6/2019 | Madison Speedway - Madison, MN 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 | - | DNS | - |
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| 7/14/2019 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Regular Race WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 7th | - | - | 17th (DNF) |
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| 7/21/2019 | Casino Speedway - Watertown, SD AFCO Race of Champions Qualifier Race Night WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 4th | - | - | 16th |
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| 8/4/2019 | Casino Speedway - Watertown, SD Advantage RV's Mod Tour Series Finale WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 6th | - | 9th | - |
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| 8/11/2019 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Weekly Race WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 6th | - | - | 19th (DNF) |
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| 8/17/2019 | Madison Speedway - Madison, MN Meet the Drivers Night Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Rain Out |
| 8/24/2019 | Madison Speedway - Madison, MN Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dean Small (WISSOTA Midwest Mods) | 6th | - | - | 15th (DNF) |
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| 8/25/2019 | Casino Speedway - Watertown, SD 10th Annual USMTS Summer Slam/Sandy Benson Memorial A Modifieds: USMTS - United States Modified Touring Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 5th | - | 4th | - |
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| 9/1/2019 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Season Championship Night WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 7th | - | - | 22nd (DNF) |
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| 9/2/2019 | Madison Speedway - Madison, MN Labor Day Season Championship Night 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) | - | - | 24th (DNF) |
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| 9/20/2019 | Casino Speedway - Watertown, SD Autumn Classic Night #1 Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 7th | - | 2nd | 19th (DNF) |
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| 9/21/2019 | Casino Speedway - Watertown, SD Autumn Classic Night #2 Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Dean Small (WISSOTA Midwest Mods) | 6th | - | 7th (DNF) | - |
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| 9/27/2019 | Madison Speedway - Madison, MN Madtown Showdown Night #1 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 | - | 7th | - |
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| 9/28/2019 | Madison Speedway - Madison, MN Madtown Showdown Night #2 Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | Dean Small (WISSOTA Midwest Mods) | 8th (DNF) | - | DNS | - |
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