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| 5/22/2020 | Miller Central Speedway - Miller, SD Make up for rainout-doubleheader Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 1st |
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| 5/23/2020 | Miller Central Speedway - Miller, SD All Classes- Sponsor TBA Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 1st |
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| 5/25/2020 | Sheyenne Speedway - Lisbon, ND MEMORIAL DAY RACE Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 5th |
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| 5/29/2020 | Miller Central Speedway - Miller, SD Double Header weekend Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 1st |
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| 5/30/2020 | Miller Central Speedway - Miller, SD All Classes- Sponsor TBA Dirt Late Models, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 2nd |
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| 5/31/2020 | Sheyenne Speedway - Lisbon, ND Weekly Racing SPECIAL Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Pure Stock) | 2nd | - | - | 2nd |
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| 6/6/2020 | Jamestown Speedway - Jamestown, ND 2020 Jamestown Speedway Season Opener & Wissota Midwest Modified Special A Modifieds, B Modifieds, Street Stocks, Semi-Pro Legends, Pure Stock, All Star Slingshots, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Street Stock, Junior Slingshots | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 2nd |
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| 6/13/2020 | Miller Central Speedway - Miller, SD Tri-State Late Model Series Dirt Late Models: Tri-State Late Models Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 1st |
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| 6/14/2020 | Sheyenne Speedway - Lisbon, ND STREET STOCK TOUR | TOP GUN MW MOD Special | Minn-Kota Legends Tour Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 1st |
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| 6/20/2020 | Jamestown Speedway - Jamestown, ND 2nd Annual Jeff Carpenter Memorial Race & RC Car Night A Modifieds, B Modifieds, Street Stocks, Semi-Pro Legends, Pure Stock, IMCA Modified, WISSOTA Midwest Mods, WISSOTA Street Stock, Junior Slingshots | Results | | Jayden Michaelsohn (Pure Stock) | 4th | - | - | 20th (DNF) |
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| 6/21/2020 | Sheyenne Speedway - Lisbon, ND FATHER'S DAY 47TH ANNIVERSARY Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Pure Stock) | 3rd | - | - | 6th |
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| 6/27/2020 | Miller Central Speedway - Miller, SD Late Model Special- $2,000 to win Pure Stock, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 2nd |
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| 6/28/2020 | Sheyenne Speedway - Lisbon, ND 2020 DAKOTA DREAM "BIGGEST Race of the Year" Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Pure Stock) | 2nd | - | - | 4th |
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| 7/4/2020 | Miller Central Speedway - Miller, SD All Classes- A Mod Special Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 6th | - | - | 1st |
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| 7/10/2020 | Tri County Speedway - Wishek, ND POWRi Minn-Kota Lightning Sprints at Tri County Speedway Lightning Sprints: POWRi Minn-Kota Lightning Sprints Hobby Stocks, Young Lions Legends, Sport Compact, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Hobby Stocks) | 1st | - | - | 1st |
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| 7/18/2020 | Miller Central Speedway - Miller, SD Street Stock Tour (All Classes) Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 1st |
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| 7/23/2020 | Tri County Speedway - Wishek, ND Hobby Stocks, Young Lions Legends, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Hobby Stocks) | 2nd | - | - | 4th |
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| 7/25/2020 | Miller Central Speedway - Miller, SD All Classes- Sponsor TBA Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 9th (DNF) |
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| 8/1/2020 | Miller Central Speedway - Miller, SD BMod special- $1,000 to win- all classes running Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 4th | - | - | 11th (DNF) |
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| 8/2/2020 | Sheyenne Speedway - Lisbon, ND KING OF THE HILL | Minn-Kota Legend Car Tour Championship Night Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Pure Stock) | 2nd | - | - | 3rd |
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| 8/8/2020 | Miller Central Speedway - Miller, SD All Classes Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 2nd | - | - | 1st |
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| 8/14/2020 | Miller Central Speedway - Miller, SD 6th Annual Big Dog Race Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 2nd | - | - | 10th |
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| 8/15/2020 | Miller Central Speedway - Miller, SD Season Championship! Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Jayden Michaelsohn (Pure Stock) | 2nd | - | - | 1st |
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| 8/16/2020 | Sheyenne Speedway - Lisbon, ND SPEEDFEST + WISSOTA MODIFIEDS Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 3rd |
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| 8/23/2020 | Sheyenne Speedway - Lisbon, ND STREET STOCK TOUR Championship Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Pure Stock) | 1st | - | - | 3rd |
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| 9/6/2020 | Sheyenne Speedway - Lisbon, ND SHEYENNE SHOWDOWN | Track Championship Pro Legends, Generic 1, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Jayden Michaelsohn (Pure Stock) | 4th | - | - | 1st |
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