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| 5/29/2023 | Sheyenne Speedway - Lisbon, ND MONDAY - MEMORIAL DAY SPECIAL Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Bo Gregor (Pro Legends) | 4th | - | - | 5th |
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| 6/8/2023 | Sheyenne Speedway - Lisbon, ND Sheyenne Speedway WISSOTA Street Stock: Street Stock Tour Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods | Results | | Bo Gregor (Pro Legends) | 2nd | - | - | 5th |
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| 6/15/2023 | Sheyenne Speedway - Lisbon, ND Sheyenne Speedway WISSOTA Modifieds: Moonshine Mod Tour Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods | Results | | Bo Gregor (Pro Legends) | 1st | - | - | 4th |
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| 6/22/2023 | Sheyenne Speedway - Lisbon, ND U.S. LEGEND CAR TOUR | MEET THE LEGEND DRIVERS Pro Legends, Sport Compact, Pure Stock, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Bo Gregor (Pro Legends) | 1st | - | - | 5th |
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| 6/29/2023 | Sheyenne Speedway - Lisbon, ND Sheyenne Speedway WISSOTA Street Stock: Street Stock Tour Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds | Results | | Bo Gregor (Pro Legends) | 2nd | - | - | 3rd |
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| 8/3/2023 | Sheyenne Speedway - Lisbon, ND Sheyenne Speedway WISSOTA Midwest Mods: Rebel Midwest Mod Tour Pro Legends, Sport Compact, Pure Stock, WISSOTA Street Stock | Results | | Bo Gregor (Pro Legends) | 5th | - | - | 4th |
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| 8/17/2023 | Sheyenne Speedway - Lisbon, ND KIDS NIGHT | LEGENDS CAR TOUR Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Bo Gregor (Pro Legends) | 3rd | - | - | 10th |
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| 8/24/2023 | Sheyenne Speedway - Lisbon, ND TRACK CHAMPIONSHIP | RANSOM COUNTY FAIR Pro Legends, Sport Compact, Pure Stock, WISSOTA Midwest Mods, WISSOTA Modifieds, WISSOTA Street Stock | Results | | Bo Gregor (Pro Legends) | 3rd | - | - | 8th |
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