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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 | | James Dragt Jr (WISSOTA Midwest Mods) | 2nd | - | - | 12th |
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| 5/31/2019 | I-94 Speedway - Fergus Falls, MN RV Advantage Mod Tour-MINNESOTA MOTORS and Kibble Equipment Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds | Results | | James Dragt Jr (WISSOTA Midwest Mods) | 5th | - | - | 20th |
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| 6/1/2019 | Madison Speedway - Madison, MN Stock Cars, Economy Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | James Dragt Jr (WISSOTA Midwest Mods) | 6th | - | - | 17th (DNF) |
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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 | | James Dragt Jr (WISSOTA Midwest Mods) | 5th | - | - | 10th |
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| 6/9/2019 | 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 | | James Dragt Jr (WISSOTA Midwest Mods) | 7th | - | 2nd | 15th |
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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 | | James Dragt Jr (WISSOTA Midwest Mods) | 6th | - | - | 16th (DNF) |
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| 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 | | James Dragt Jr (WISSOTA Midwest Mods) | 7th (DNF) | - | - | DNS |
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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 | | James Dragt Jr (WISSOTA Midwest Mods) | 6th | - | 3rd | 22nd |
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| 7/12/2019 | Fiesta City Speedway - Montevideo, MN Hornet Special Factory Stocks, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock, WISSOTA Hornet | Results | | James Dragt Jr (WISSOTA Midwest Mods) | 7th | - | - | 10th |
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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 | | James Dragt Jr (WISSOTA Midwest Mods) | 4th | - | - | 12th |
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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 | | James Dragt Jr (WISSOTA Midwest Mods) | 6th (DNF) | - | - | DNS |
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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 | | James Dragt Jr (WISSOTA Midwest Mods) | 7th (DNF) | - | - | 20th (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 | | James Dragt Jr (WISSOTA Midwest Mods) | 7th (DNF) | - | DNS | - |
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