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| 5/8/2021 | Jackpine Gypsies - Sturgis, SD Thomas & Sons Moving Company Race Night Rookie Class: Black Hills Kart Racing Winged A-Class, Junior 1 Medium Dirt Karts, Junior 2 Medium Dirt Karts, Adult Open, Adult Medium, Junior 3 Medium Dirt Karts, Red Rookie | Results | | Sean McHenry (Junior 3 Medium Dirt Karts) | 1st | - | - | 1st |
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| 6/12/2021 | Jackpine Gypsies - Sturgis, SD Winged A-Class: NOW600 A-Class Micros Rookie Class: Black Hills Kart Racing Junior 1 Medium Dirt Karts, Junior 2 Medium Dirt Karts, Adult Open, Adult Medium, Junior 3 Medium Dirt Karts, Red Rookie | Results | | Sean McHenry (Junior 3 Medium Dirt Karts) | 1st | - | - | 2nd |
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| 6/26/2021 | Jackpine Gypsies - Sturgis, SD Black Hills Paintless Dent Repair Race Night Rookie Class: Black Hills Kart Racing Winged A-Class, Junior 1 Medium Dirt Karts, Junior 2 Medium Dirt Karts, Adult Open, Adult Medium, Junior 3 Medium Dirt Karts, Red Rookie | Results | | Sean McHenry (Junior 3 Medium Dirt Karts) | 7th | - | - | 1st |
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| 7/10/2021 | Jackpine Gypsies - Sturgis, SD Black Hills Doors Race Night Rookie Class: Black Hills Kart Racing Winged A-Class, Junior 1 Medium Dirt Karts, Junior 2 Medium Dirt Karts, Adult Open, Adult Medium, Junior 3 Medium Dirt Karts, Red Rookie | Results | | Sean McHenry (Junior 3 Medium Dirt Karts) | 1st | - | - | 1st |
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| 7/24/2021 | Jackpine Gypsies - Sturgis, SD Winged A-Class: NOW600 A-Class Micros Rookie Class: Black Hills Kart Racing Junior 1 Medium Dirt Karts, Junior 2 Medium Dirt Karts, Adult Open, Adult Medium, Junior 3 Medium Dirt Karts, Red Rookie | Results | | Sean McHenry (Junior 3 Medium Dirt Karts) | 4th | - | - | 1st |
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| 9/10/2021 | Jackpine Gypsies - Sturgis, SD Winged A-Class: NOW600 A-Class Micros Rookie Class: Black Hills Kart Racing Junior 1 Medium Dirt Karts, Junior 2 Medium Dirt Karts, Adult Open, Adult Medium, Junior 3 Medium Dirt Karts, Red Rookie | Results | | Sean McHenry (Junior 3 Medium Dirt Karts) | 1st | - | - | 5th |
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| 9/11/2021 | Jackpine Gypsies - Sturgis, SD Winged A-Class: NOW600 A-Class Micros Rookie Class: Black Hills Kart Racing Junior 1 Medium Dirt Karts, Junior 2 Medium Dirt Karts, Adult Open, Adult Medium, Junior 3 Medium Dirt Karts, Red Rookie | Results | | Sean McHenry (Junior 3 Medium Dirt Karts) | 3rd | - | - | 1st |
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| 11/27/2021 | James Kjerstad Event Center - Rapid City, SD The Gobbler Indoor Kart Championship Rookie Class: Black Hills Kart Racing Junior 1 Medium Dirt Karts, Junior 2 Medium Dirt Karts, Junior 2 Heavy Dirt Karts, Adult Open, Adult Heavy, Adult Medium, Junior 3 Medium Dirt Karts | Results | | Sean McHenry (Junior 3 Medium Dirt Karts) | 3rd | 3rd | - | 3rd |
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