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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 | | Kyle Bertram (WISSOTA Street Stock) | 4th | - | - | 3rd |
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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 | | Kyle Bertram (WISSOTA Street Stock) | 4th | - | - | 16th (DNF) |
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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 | | Kyle Bertram (WISSOTA Street Stock) | 5th | - | - | 8th |
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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 | | Kyle Bertram (WISSOTA Street Stock) | 2nd | - | - | 3rd |
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| 5/31/2020 | Casino Speedway - Watertown, SD WISSOTA Dirt Track Series Weekly Racing Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Bertram (WISSOTA Street Stock) | 5th | - | - | 8th |
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| 6/5/2020 | Brown County Speedway - Aberdeen, SD Structural Buildings WISSOTA Late Model Challenge Series WISSOTA Late Model: Wissota Late Model Challenge Series WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Bertram (WISSOTA Street Stock) | 6th | - | - | 17th (DNF) |
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| 6/11/2020 | Tri County Speedway - Wishek, ND Season opener Hobby Stocks, Stock Cars, Young Lions Legends, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Kyle Bertram (WISSOTA Street Stock) | 6th | - | - | 10th |
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| 6/12/2020 | Brown County Speedway - Aberdeen, SD BCS 06/12/2020 Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Bertram (WISSOTA Street Stock) | 7th (DNF) | - | - | 10th (DNF) |
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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 | | Kyle Bertram (WISSOTA Street Stock) | 2nd | - | - | 7th |
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| 6/21/2020 | Casino Speedway - Watertown, SD Fathers Day WISSOTA Dirt Track Series Weekly Series Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Bertram (WISSOTA Street Stock) | 6th | - | - | 19th (DNF) |
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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 | | Kyle Bertram (WISSOTA Street Stock) | 7th (DNF) | - | 10th | - |
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| 8/21/2020 | Black Hills Speedway - Rapid City, SD Points Championship & WISSOTA R.O.C Night 360 Sprints - Non-Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Kyle Bertram (360 Sprints - Non-Winged) | - | - | - | - | | Kyle Bertram (WISSOTA Street Stock) | 3rd | - | - | 12th (DNF) |
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| 8/22/2020 | Dakota State Fair Speedway - Huron, SD World of Outlaws NOS Energy Drink Sprint Cars WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Kyle Bertram (WISSOTA Street Stock) | 1st | - | - | 2nd |
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| 8/28/2020 | Black Hills Speedway - Rapid City, SD Rushmore Outlaw Showdown 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Kyle Bertram (WISSOTA Street Stock) | 5th (DNF) | - | - | 3rd |
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| 8/29/2020 | Black Hills Speedway - Rapid City, SD Annual HALF-MILE NATIONALS IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Late Model, WISSOTA Street Stock | Results | | Kyle Bertram (WISSOTA Street Stock) | 2nd | - | - | DNS |
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