| Player Tournament Awards | Players Name | Plays For | Stature | Tournament | Season |
| Defensive Tournament MVP | Brett Rowan | OSS/Thunder Gun Express | League | 3rd Matthew Quigley Memorial Q44 Open | 2023 |
| All Tournament Team | David Burns | OSS/Thunder Gun Express | League | 3rd Matthew Quigley Memorial Q44 Open | 2023 |
|
| All Tournament Team | Ben Lacasse | Rocky Hill Farm/ Holliston Sewer | State Level 2 - USSSA | 25th Annual Marucci Firecracker Classic | 2025 |
| All Tournament Team | Scott Mello | Rocky Hill Farm/ Holliston Sewer | State Level 2 - USSSA | 25th Annual Marucci Firecracker Classic | 2025 |
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| All Tournament Team | David Burns | Ellis Painting | NIT - USSSA - Berth | Rose City Rumble D NIT | 2025 |
| All Tournament Team | David Burns | Ellis Painting | NIT - USSSA - Berth | Rose City Rumble D NIT | 2025 |
| All Tournament Team | David Burns | Ellis Painting | NIT - USSSA - Berth | Rose City Rumble D NIT | 2025 |
|
| All Tournament Team | Andrew Barbosa | Woo City Wolf Pack | NIT - USSSA - Points | Wishes Candle D NIT | 2024 |
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| All Tournament Team | David Burns | Ellis Painting | NIT - USSSA - Points | Wishes Candle D NIT | 2025 |
| All Tournament Team | David Burns | MB Flooring | NIT - USSSA - Points | Wishes Candle D NIT | 2025 |
| All Tournament Team | David Burns | Ellis Painting | NIT - USSSA - Points | Wishes Candle D NIT | 2025 |
|
| All Tournament Team | Ben Lacasse | Rocky Hill Farm/ Holliston Sewer | NIT - USSSA - Points | Central Mass D NIT | 2025 |
| All Tournament Team | Scott Mello | Rocky Hill Farm/ Holliston Sewer | NIT - USSSA - Points | Central Mass D NIT | 2025 |
|
| All Tournament Team | Ben Lacasse | Farmyard Flushers/Kawaii | NIT - USSSA - Points | National Gold D NIT | 2026 |
|
| Tournament MVP | Ben Lacasse | Farmyard Flushers/Kawaii | NIT - USSSA - Points | OSS Apparel D NIT | 2026 |
|
| All Tournament Team | Ben Lacasse | Farmyard Flushers/Kawaii | NIT - USSSA - Points | Memorial Day D NIT | 2026 |
|
| Defensive Tournament CO-MVP | Brett Rowan | Woo City Wolf Pack | State - USSSA | Men's D State Tournament | 2025 |
|
| All Tournament Team | Brett Rowan | Angry Shamrocks | State - GSL | New England Region D/E States | 2024 |
| All Tournament Team | Brett Rowan | Angry Shamrocks | State - GSL | New England Region D/E States | 2024 |
| All Tournament Team | Brett Rowan | Bombers | State - GSL | New England Region D/E States | 2024 |
| All Tournament Team | Brett Rowan | Angry Shamrocks | State - GSL | New England Region D/E States | 2024 |
| All Tournament Team | Brett Rowan | Woo City Wolf Pack | State - GSL | New England Region D/E States | 2024 |
|
| All Tournament Team | Matthew Collins | Deeply Kneaded | State Level 2 - USSSA | Lil Firecracker | 2020 |
|
| All Tournament Team | Ray Branco | TPS/DEEPLY KNEADED, LLC | Qualifier - USSSA - Points | NH Men’s E Qualifier | 2024 |
| All Tournament Team | Matthew Collins | TPS/DEEPLY KNEADED, LLC | Qualifier - USSSA - Points | NH Men’s E Qualifier | 2024 |
| All Tournament Team | Matthew Collins | TPS/DEEPLY KNEADED, LLC | Qualifier - USSSA - Points | NH Men’s E Qualifier | 2024 |
| All Tournament Team | Michael Lingley | TPS/DEEPLY KNEADED, LLC | Qualifier - USSSA - Points | NH Men’s E Qualifier | 2024 |
| All Tournament Team | Michael Lingley | TPS/DEEPLY KNEADED, LLC | Qualifier - USSSA - Points | NH Men’s E Qualifier | 2024 |
|
| All Tournament Team | Scott Mello | Rocky Hill Farm/ Holliston Sewer | Qualifier - USSSA - Points | NE Men's E World Warmup Travel Money | 2025 |
|
| All Tournament Team | James Caisse | DSI | NIT - USSSA - Berth | Easton NE Shootout E NIT | 2017 |
|
| Tournament MVP | Chad McIntosh | Hassa | NIT - USSSA - Berth | Bang 4 Your $ E NIT | 2018 |
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| All Tournament Team | Matthew Collins | Riva Ratz/ Cos Apparel | NIT - USSSA - Berth | D&M Designs E NIT | 2019 |
| All Tournament Team | Matthew Collins | Riva Ratz/ Cos Apparel | NIT - USSSA - Berth | D&M Designs E NIT | 2019 |
|
| All Tournament Team | James Caisse | Deeply Kneaded | NIT - USSSA - Berth | Two Guys Sports E NIT | 2020 |
| All Tournament Team | Matthew Collins | Deeply Kneaded | NIT - USSSA - Berth | Two Guys Sports E NIT | 2020 |
| All Tournament Team | Colton Furtado | Deeply Kneaded | NIT - USSSA - Berth | Two Guys Sports E NIT | 2020 |
|
| All Tournament Team | James Caisse | Kings Clothing Club/TGE | NIT - USSSA - Berth | OSS/D&M Designs E NIT | 2021 |
| All Tournament Team | James Caisse | Kings Clothing Club/TGE | NIT - USSSA - Berth | OSS/D&M Designs E NIT | 2021 |
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| All Tournament Team | David Burns | OSS/Thunder Gun Express | NIT - USSSA - Berth | Dudley Sports E NIT | 2023 |
| All Tournament Team | David Burns | OSS/Thunder Gun Express | NIT - USSSA - Berth | Dudley Sports E NIT | 2023 |
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| All Tournament Team | James Caisse | Whaling City Crew | NIT - USSSA - Berth | Central Mass E NIT | 2026 |
|
| Offensive Tournament MVP | James Caisse | Deeply Kneaded | NIT - USSSA - Points | OSS/Reflections Fall Fest | 2020 |
|
| Offensive Tournament MVP | Scott Mello | D2Sports/OSS | NIT - USSSA - Points | OSS/Silver City E NIT | 2022 |
| All Tournament Team | Chad McIntosh | D2Sports/OSS | NIT - USSSA - Points | OSS/Silver City E NIT | 2022 |
|
| Tournament CO-MVP | Ben Lacasse | Deeply Kneaded LLC | NIT - USSSA - Points | OSS/Reflections E NIT | 2022 |
| All Tournament Team | Michael Lingley | Deeply Kneaded LLC | NIT - USSSA - Points | OSS/Reflections E NIT | 2022 |
| All Tournament Team | Brett Rowan | D2Sports/OSS | NIT - USSSA - Points | OSS/Reflections E NIT | 2022 |
|
| All Tournament Team | David Burns | D2Sports/OSS | NIT - USSSA - Points | OSS Memorial Day E NIT | 2022 |
| All Tournament Team | David Burns | D2Sports/OSS | NIT - USSSA - Points | OSS Memorial Day E NIT | 2022 |
| All Tournament Team | James Caisse | D2Sports/OSS | NIT - USSSA - Points | OSS Memorial Day E NIT | 2022 |
|
| All Tournament Team | David Burns | D2Sports/OSS | NIT - USSSA - Points | OSS/Independence Day E NIT | 2022 |
| All Tournament Team | David Burns | D2Sports/OSS | NIT - USSSA - Points | OSS/Independence Day E NIT | 2022 |
| All Tournament Team | Scott Mello | D2Sports/OSS | NIT - USSSA - Points | OSS/Independence Day E NIT | 2022 |
| All Tournament Team | Andrew Walski | D2Sports/OSS | NIT - USSSA - Points | OSS/Independence Day E NIT | 2022 |
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| All Tournament Team | Chad McIntosh | OSS/Thunder Gun Express | NIT - USSSA - Points | OSS Memorial Day E NIT | 2023 |
| All Tournament Team | Chad McIntosh | OSS/Thunder Gun Express | NIT - USSSA - Points | OSS Memorial Day E NIT | 2023 |
| All Tournament Team | Brett Rowan | OSS/Thunder Gun Express | NIT - USSSA - Points | OSS Memorial Day E NIT | 2023 |
| All Tournament Team | Brett Rowan | OSS/Thunder Gun Express | NIT - USSSA - Points | OSS Memorial Day E NIT | 2023 |
| All Tournament Team | Brett Rowan | OSS/Thunder Gun Express | NIT - USSSA - Points | OSS Memorial Day E NIT | 2023 |
|
| Tournament CO-MVP | Matthew Collins | Deeply Kneaded, LLC | NIT - USSSA - Points | National Gold E NIT | 2023 |
| Tournament CO-MVP | Matthew Collins | Deeply Kneaded, LLC | NIT - USSSA - Points | National Gold E NIT | 2023 |
|
| All Tournament Team | Ray Branco | Deeply Kneaded, LLC | NIT - USSSA - Points | NH Men’s E NIT | 2023 |
| All Tournament Team | Ray Branco | Deeply Kneaded, LLC | NIT - USSSA - Points | NH Men’s E NIT | 2023 |
| All Tournament Team | Matthew Collins | Deeply Kneaded, LLC | NIT - USSSA - Points | NH Men’s E NIT | 2023 |
| All Tournament Team | Matthew Collins | Deeply Kneaded, LLC | NIT - USSSA - Points | NH Men’s E NIT | 2023 |
| All Tournament Team | Michael Lingley | Deeply Kneaded, LLC | NIT - USSSA - Points | NH Men’s E NIT | 2023 |
| All Tournament Team | Michael Lingley | Harts construction/1more softball | NIT - USSSA - Points | NH Men’s E NIT | 2023 |
| All Tournament Team | Michael Lingley | Deeply Kneaded, LLC | NIT - USSSA - Points | NH Men’s E NIT | 2023 |
| All Tournament Team | Michael Lingley | Harts construction/1more softball | NIT - USSSA - Points | NH Men’s E NIT | 2023 |
|
| All Tournament Team | Scott Mello | PSC | NIT - USSSA - Points | Memorial Day E NIT | 2024 |
| All Tournament Team | Scott Mello | TPS/DEEPLY KNEADED, LLC | NIT - USSSA - Points | Memorial Day E NIT | 2024 |
| All Tournament Team | Scott Mello | TPS/DEEPLY KNEADED, LLC | NIT - USSSA - Points | Memorial Day E NIT | 2024 |
|
| All Tournament Team | Scott Mello | Rocky Hill Farm/ Holliston Sewer | NIT - USSSA - Points | South Coast E NIT | 2025 |
|
| All Tournament Team | Ben Lacasse | Rocky Hill Farm/ Holliston Sewer | NIT - USSSA - Points | Wishes Candle E NIT | 2025 |
|
| All Tournament Team | Chad McIntosh | HASSA | State - USSSA | Mass Men's E States | 2017 |
|
| Offensive Tournament MVP | Andrew Walski | OSS Mules | State - USSSA | RI/MA Men's E State Tournament | 2020 |
| All Tournament Team | James Caisse | Deeply Kneaded | State - USSSA | RI/MA Men's E State Tournament | 2020 |
|
| All Tournament Team | Matthew Collins | Cool Runnings | State - USSSA | Rhode Island Men's E State Tournament | 2021 |
| All Tournament Team | Matthew Collins | Deeply Kneaded | State - USSSA | Rhode Island Men's E State Tournament | 2021 |
|
| All Tournament Manager | James Caisse | Kings Clothing Club/TGE | State - USSSA | Mass Men's E State Tournament | 2021 |
| All Tournament Team | Andrew Barbosa | Pink Sox | State - USSSA | Mass Men's E State Tournament | 2021 |
| All Tournament Team | James Caisse | Kings Clothing Club/TGE | State - USSSA | Mass Men's E State Tournament | 2021 |
|
| All Tournament Manager | James Caisse | D2Sports/OSS | State - USSSA | Men's E State Tournament | 2022 |
|
| Tournament MVP | Brett Rowan | OSS/Thunder Gun Express | State - USSSA | Men's E State Tournament | 2023 |
| Tournament MVP | Brett Rowan | OSS/Thunder Gun Express | State - USSSA | Men's E State Tournament | 2023 |
| All Tournament Team | Andrew Walski | OSS/Thunder Gun Express | State - USSSA | Men's E State Tournament | 2023 |
|
| All Tournament Team | Matthew Collins | TPS/DEEPLY KNEADED, LLC | State - USSSA | Men's E State Tournament | 2024 |
|
| Tournament CO-MVP | Scott Mello | PSC | State - GSL | New England Region D/E States | 2024 |
| Tournament CO-MVP | Scott Mello | TPS/DEEPLY KNEADED, LLC | State - GSL | New England Region D/E States | 2024 |
| Tournament CO-MVP | Scott Mello | TPS/DEEPLY KNEADED, LLC | State - GSL | New England Region D/E States | 2024 |
|
| Tournament CO-MVP | David Burns | D2Sports/OSS | State Level 2 - USSSA | NH Men’s E Beast of East 5gg | 2022 |
| Tournament CO-MVP | David Burns | D2Sports/OSS | State Level 2 - USSSA | NH Men’s E Beast of East 5gg | 2022 |
| All Tournament Team | James Caisse | D2Sports/OSS | State Level 2 - USSSA | NH Men’s E Beast of East 5gg | 2022 |
| All Tournament Team | Brett Rowan | D2Sports/OSS | State Level 2 - USSSA | NH Men’s E Beast of East 5gg | 2022 |
|
| All Tournament Team | Brett Rowan | Another Double/MB Flooring | State Level 2 - USSSA | NH Men’s E Beast of East 4gg | 2026 |
|
| All Tournament Team | Matthew Collins | Deeply Kneaded LLC | Regional - USSSA | Mens E Northeast National - Alter Ego Sports | 2022 |
|
| All Tournament Team | Ben Lacasse | Rocky Hill Farm/ Holliston Sewer | Regional - USSSA | Mens NE E Regional | 2025 |
|
| All Tournament Team | Matthew Collins | TPS/DEEPLY KNEADED, LLC | World - USSSA | USSSA West World Championship | 2024 |
|
| All Tournament Team | Ben Lacasse | Summit | State Level 2 - USSSA | 11th Annual Marucci Mixed Firecracker | 2026 |
|
| All Tournament Team | Matthew Collins | Metrowest Mayhem | Qualifier - USSSA - Points | Coed 3Some - First Date | 2019 |
| All Tournament Team | Matthew Collins | Metrowest Mayhem | Qualifier - USSSA - Points | Coed 3Some - First Date | 2019 |
|
| Tournament CO-MVP | James Caisse | Misfits | State - USSSA | Mass Mixed E States | 2018 |
| All Tournament Team | Matthew Collins | Misfits | State - USSSA | Mass Mixed E States | 2018 |