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| 5/7/2021 | Black Hills Speedway - Rapid City, SD Opening Night $ Month of Money $ Series Begins 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 2nd | - | - | 6th |
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| 5/14/2021 | Black Hills Speedway - Rapid City, SD $ Month of Money $ Series 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 4th | - | - | 13th (DNF) |
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| 5/28/2021 | Black Hills Speedway - Rapid City, SD $ Month of Money $ Series 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 5th | - | - | 9th |
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| 5/29/2021 | Bandit Speedway - Box Elder, SD Race Night A Modifieds, Non-Winged Sprints, WISSOTA Midwest Mods, WISSOTA Late Model | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 3rd | - | - | 3rd |
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| 6/4/2021 | Black Hills Speedway - Rapid City, SD PACK THE STANDS! $ Month Of Money $ Series Finale 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 5th | - | - | 5th |
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| 6/18/2021 | Black Hills Speedway - Rapid City, SD Dillon Heinzerling Midwest Mod Memorial Race IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 5th | - | - | 11th |
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| 6/26/2021 | Miller Central Speedway - Miller, SD Regular Races Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 2nd | - | - | 7th |
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| 7/2/2021 | Black Hills Speedway - Rapid City, SD FIREWORKS Special! 360 Sprint Cars, Wissota Street Stock, IMCA Hobby Stock, Wissota Mod 4 Specials 360 Sprints - Winged, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 4th | - | - | 4th |
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| 7/3/2021 | Miller Central Speedway - Miller, SD 4th of July Special Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 1st | - | - | 7th |
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| 7/9/2021 | Black Hills Speedway - Rapid City, SD WISSOTA Midwest Mod Border Clash 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 3rd | - | - | 8th (DNF) |
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| 7/23/2021 | Black Hills Speedway - Rapid City, SD High Plains Late Model Tour 360 Sprints - Winged, Dirt Super Late Models, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 6th | - | - | - |
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| 7/24/2021 | Miller Central Speedway - Miller, SD Street Stock Special Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Late Model, WISSOTA Street Stock, WISSOTA Super Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 5th | - | - | 10th (DNF) |
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| 7/30/2021 | Black Hills Speedway - Rapid City, SD Regular Race 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 3rd | - | - | 9th (DNF) |
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| 8/20/2021 | Black Hills Speedway - Rapid City, SD Points Championship Night WISSOTA R.O.C 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 5th (DNF) | - | - | 6th |
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| 9/3/2021 | Gillette Thunder Speedway - Gillette, WY 21ST ANNUAL EAST-WEST CLASH IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Late Model, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 4th | - | 5th | - |
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| 9/10/2021 | Black Hills Speedway - Rapid City, SD South Dakota Lottery Half-Mile Nationals 360 Sprints - Winged, IMCA Modified, IMCA Hobby Stock, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Brandon Woodhead (WISSOTA Midwest Mods) | 5th | - | - | 9th |
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