| | Heat | Dash | B Feature | A Feature |
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| 6/6/2019 | Black Hills Speedway - Rapid City, SD 2 Day Show!! 305 Sprints - Winged, Hobby Stocks, A Modifieds, Dirt Late Models, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Randy Dolberg (305 Sprints - Winged) | 6th (DNF) | - | - | DNS |
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| 6/15/2019 | Black Hills Speedway - Rapid City, SD 360 Sprints - Winged: ASCS National with ASCS Frontier Region Hobby Stocks, WISSOTA Street Stock | Results | | Randy Dolberg (360 Sprints - Winged) | 5th | - | 4th | 20th (DNF) |
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| 7/26/2019 | Black Hills Speedway - Rapid City, SD 360 Sprints - Winged: ASCS Frontier Region Hobby Stocks, WISSOTA Midwest Mods, WISSOTA Street Stock | Results | | Randy Dolberg (360 Sprints - Winged) | 4th | - | - | 11th |
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| 7/27/2019 | Gillette Thunder Speedway - Gillette, WY 360 Sprints - Winged: ASCS Frontier Region Hobby Stocks, WISSOTA Midwest Mods, WISSOTA Mod Four, WISSOTA Street Stock | Results | | Randy Dolberg (360 Sprints - Winged) | 7th | - | - | DNS |
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| 8/9/2019 | Sweetwater Speedway - Rock Springs, WY 360 Sprints - Winged: ASCS Frontier Region A Modifieds, B Modifieds, Street Stocks, 250 yamaha, Asphalt Street Stocks | Results | | Randy Dolberg (360 Sprints - Winged) | 5th | - | - | 6th |
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| 8/10/2019 | Sweetwater Speedway - Rock Springs, WY 360 Sprints - Winged: ASCS Frontier Region A Modifieds, B Modifieds, Street Stocks, 250 yamaha, Asphalt Street Stocks | Results | | Randy Dolberg (360 Sprints - Winged) | 6th | - | - | 7th |
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| 8/23/2019 | Black Hills Speedway - Rapid City, SD 410 Sprints - Winged: World of Outlaws Hobby Stocks, WISSOTA Street Stock | Results | | Randy Dolberg (410 Sprints - Winged) | 9th | - | 14th | 18th |
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