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| Player Tournament Awards | Players Name | Plays For | Stature | Tournament | Season | |
| All State Showcase Nominee | Xavier Headen | Olney Pirates | Qualifier | First Pitch Classic | 2020 | |
| Game MVP | Joshua Johnson | Olney Buccaneers 14U | Qualifier | 4th of July Classic | 2021 | |
| Outstanding Pitcher | Xavier Headen | Olney Pirates | Qualifier | King of the Rock | 2020 | |
| Game MVP | Xavier Headen | Olney Pirates | Qualifier | Turf Wars-I | 2019 | |
| All State Showcase Nominee | Xavier Headen | Olney Pirates | Qualifier | Turf Wars-II | 2019 | |
| Game MVP | Xavier Headen | Olney Pirates | Qualifier | Spring Training Classic | 2018 | |