| Player Tournament Awards | Players Name | Plays For | Stature | Tournament | Season |
| All Tournament Team | Brandyn Ladetto | LFT/SIMONELLI’S TOWING | Qualifier - USSSA - Points | 3rd Matthew Quigley Memorial Q44 Open | 2023 |
|
| All Tournament Team | stephen Bailey | ChecKing/Alter Ego/Miller Carting | NIT - USSSA - Points | 16th Annual Northeast Shootout | 2026 |
| All Tournament Team | stephen Bailey | AUIT/DeMieri Properties/Big Dawg | NIT - USSSA - Points | 16th Annual Northeast Shootout | 2026 |
| All Tournament Team | stephen Bailey | ChecKing/Alter Ego/Miller Carting | NIT - USSSA - Points | 16th Annual Northeast Shootout | 2026 |
| All Tournament Team | stephen Bailey | ChecKing/Alter Ego/Miller Carting | NIT - USSSA - Points | 16th Annual Northeast Shootout | 2026 |
|
| Tournament MVP | Erik Dralle | LFG | Qualifier - USSSA - Points | BOMBS away | 2020 |
|
| All Tournament Team | stephen Bailey | RDD/AZ/Webby/BigDawg/GameUp | NIT - USSSA - Points | The Jimmy Dogs Memorial - NIT | 2022 |
|
| All Tournament Team | Chris Bishop | Checking/Worth | State - USSSA | N.E. State B Championship | 2007 |
|
| All Tournament Team | Richard Countryman | Sharks/OSS Apparel | Qualifier - USSSA - Points | Men's March Madness | 2020 |
| All Tournament Team | Bobby Pentino | Sharks/OSS Apparel | Qualifier - USSSA - Points | Men's March Madness | 2020 |
|
| All Tournament Team | stephen Bailey | RDD/SheGone/RIOT | Qualifier - USSSA - Points | Summer Classic | 2020 |
|
| All Tournament Team | stephen Bailey | RDD/AZ/Webby/BigDawg/GameUp | Qualifier - USSSA - Points | Orange Hammer Early Bird | 2022 |
|
| All Tournament Team | stephen Bailey | AZ Roofing/Big Dawg/Game Up | NIT - USSSA - Points | D&M Designs C NIT | 2023 |
| All Tournament Team | stephen Bailey | AZ Roofing/Big Dawg/Game Up | NIT - USSSA - Points | D&M Designs C NIT | 2023 |
|
| All Tournament Team | stephen Bailey | SST/TES/PTE/Michelob Ultra | NIT - USSSA - Points | Two Guys Sports C NIT | 2024 |
|
| All Tournament Team | Bobby Pentino | RDD/Chicago Sams | State Level 2 - USSSA | Beast Of The East | 2016 |
|
| All Tournament Team | Chris Bishop | Cornerstone Contractors | Regional - USSSA | Northeast C National | 2006 |
|
| All Tournament Team | stephen Bailey | RDD/AZ/Webby/BigDawg/GameUp | Regional - USSSA | Mens C Northeast National | 2022 |
|
| Tournament CO-MVP | Bobby Pentino | RDD/Chicago Sams | Qualifier - USSSA - Points | Western Mass D NIT | 2016 |
|
| All Tournament Team | Chris Bishop | Riot2k/Globe Cleaners/Barberino | Qualifier - USSSA - Points | Easton Sports D NIT #1 | 2016 |
|
| All Tournament Team | Chris Bishop | Riot2k/Globe Cleaners/Barberino | Qualifier - USSSA - Points | Mens D Northeast National | 2016 |
|
| All Tournament Manager | Bobby Pentino | LMD Hauling/Sharks/OSS | Qualifier - USSSA - Points | Men's Blast Off | 2020 |
| All Tournament Team | Richard Countryman | LMD Hauling/Sharks/OSS | Qualifier - USSSA - Points | Men's Blast Off | 2020 |
| All Tournament Team | Erik Dralle | LFG | Qualifier - USSSA - Points | Men's Blast Off | 2020 |
| All Tournament Team | Michael Komendowski | LMD Hauling/Sharks/OSS | Qualifier - USSSA - Points | Men's Blast Off | 2020 |
|
| All Tournament Team | Richard Countryman | LMD Hauling/Sharks/OSS | Qualifier - USSSA - Points | Men's NE D Championship | 2020 |
| All Tournament Team | Michael Komendowski | LMD Hauling/Sharks/OSS | Qualifier - USSSA - Points | Men's NE D Championship | 2020 |
|
| Tournament MVP | stephen Bailey | RDD/Webby/RIOT | Qualifier - USSSA - Points | Men's Let it Fly | 2021 |
| All Tournament Team | Brandyn Ladetto | RDD/Webby/RIOT | Qualifier - USSSA - Points | Men's Let it Fly | 2021 |
|
| All Tournament Team | stephen Bailey | RDD/Webby/RIOT | Qualifier - USSSA - Points | Mens D NE Championships | 2021 |
|
| Tournament MVP | Joe Guardia | Full Send/Fades Away/Yolked/OSS | Qualifier - USSSA - Points | 22nd Annual Winter Wake Up sponsored by Alter Ego | 2022 |
|
| All Tournament Team | Bobby Pentino | L.A.S. | Qualifier - USSSA - Points | Men's D NE Championships | 2024 |
|
| All Tournament Team | Matt Angelillo | L.A.S. | Qualifier - USSSA - Points | Mens 4 Pack | 2026 |
| All Tournament Team | Bobby Pentino | L.A.S. | Qualifier - USSSA - Points | Mens 4 Pack | 2026 |
|
| All Tournament Team | Matt Angelillo | L.A.S. | Qualifier - USSSA - Points | Mens Friday Night Lights | 2026 |
| All Tournament Team | Bobby Pentino | L.A.S. | Qualifier - USSSA - Points | Mens Friday Night Lights | 2026 |
|
| All Tournament Team | Bobby Pentino | Country Tavern | NIT - USSSA - Berth | Reebok Sports D NIT#1 | 2013 |
| All Tournament Team | Bobby Pentino | Pick Me | NIT - USSSA - Berth | Reebok Sports D NIT#1 | 2013 |
| All Tournament Team | Bobby Pentino | Just Bring It | NIT - USSSA - Berth | Reebok Sports D NIT#1 | 2013 |
|
| All Tournament Team | Bobby Pentino | Country Tavern | NIT - USSSA - Berth | Dudley Sports Super D NIT | 2013 |
| All Tournament Team | Bobby Pentino | Just Bring It | NIT - USSSA - Berth | Dudley Sports Super D NIT | 2013 |
|
| All Tournament Team | Bobby Pentino | Country Tavern/Chicago Sams | NIT - USSSA - Berth | Early Bird D NIT #1 | 2014 |
|
| All Tournament Team | Bobby Pentino | Country Tavern/Chicago Sams | NIT - USSSA - Berth | Easton D NIT | 2014 |
|
| All Tournament Team | Richard Countryman | Globo Gym/Shark Sports | NIT - USSSA - Berth | 2 Guys Sports Solutions D NIT | 2017 |
| All Tournament Team | Bobby Pentino | Globo Gym/Shark Sports | NIT - USSSA - Berth | 2 Guys Sports Solutions D NIT | 2017 |
|
| All Tournament Team | Bobby Pentino | Globo Gym/Shark Sports | NIT - USSSA - Berth | Easton NE Shootout D NIT | 2017 |
|
| All Tournament Team | Richard Countryman | Shark Sports/Funny Farm/Robeks | NIT - USSSA - Berth | Two Guys Sports D NIT | 2018 |
| All Tournament Team | Michael Fesko | Shark Sports/Funny Farm/Robeks | NIT - USSSA - Berth | Two Guys Sports D NIT | 2018 |
|
| All Tournament Team | stephen Bailey | Shark Sports/Funny Farm/Robeks | NIT - USSSA - Berth | RIOT Sports NE Shootout D NIT | 2018 |
| All Tournament Team | Adam Bisson | Shark Sports/Funny Farm/Robeks | NIT - USSSA - Berth | RIOT Sports NE Shootout D NIT | 2018 |
| All Tournament Team | Michael Fesko | Shark Sports/Funny Farm/Robeks | NIT - USSSA - Berth | RIOT Sports NE Shootout D NIT | 2018 |
|
| All Tournament Team | stephen Bailey | MJV/HEO sports | NIT - USSSA - Berth | Two Guys Sports D NIT | 2019 |
|
| All Tournament Team | Joe Guardia | E.M.B\deadskunks | NIT - USSSA - Berth | Rose City Rumble D NIT | 2019 |
| All Tournament Team | Joe Guardia | E.M.B\deadskunks | NIT - USSSA - Berth | Rose City Rumble D NIT | 2019 |
|
| All Tournament Team | Luis Lopez | 6th Boro / Falcone Consulting FCES | NIT - USSSA - Berth | Riot Sports NE Shootout D NIT | 2019 |
| All Tournament Team | Luis Lopez | 6th Boro / Falcone Consulting FCES | NIT - USSSA - Berth | Riot Sports NE Shootout D NIT | 2019 |
|
| All Tournament Team | stephen Bailey | RDD/SheGone/RIOT | NIT - USSSA - Berth | Easton Sports D NIT | 2020 |
|
| All Tournament Team | stephen Bailey | RDD/Webby/RIOT | NIT - USSSA - Berth | Riot Sports D NIT | 2021 |
|
| All Tournament Team | Brandyn Ladetto | RDD/Webby/RIOT | NIT - USSSA - Berth | Rose City Rumble D NIT | 2021 |
|
| All Tournament Team | Michael McGonigle | Full Send/Fades Away/OSS Apparel | NIT - USSSA - Berth | McWorld's D NIT | 2021 |
| All Tournament Team | Michael McGonigle | New Era Wolfpack | NIT - USSSA - Berth | McWorld's D NIT | 2021 |
|
| All Tournament Team | Joe Guardia | Full Send/Fades Away/Yolked/OSS | NIT - USSSA - Berth | Easton Sports D NIT | 2022 |
|
| All Tournament Team | Bobby Pentino | L.A.S. | NIT - USSSA - Berth | Northeast Shootout D NIT | 2023 |
|
| All Tournament Team | Brandyn Ladetto | Ellis Painting/Lawn Order/Team Roso | NIT - USSSA - Berth | Marucci Sports D NIT | 2026 |
|
| All Tournament Team | Joe Guardia | Full Send/Fades Away/OSS Apparel | NIT - USSSA - Points | OSS/DAO Electric D NIT | 2021 |
| All Tournament Team | Joe Guardia | Full Send/Fades Away/OSS Apparel | NIT - USSSA - Points | OSS/DAO Electric D NIT | 2021 |
|
| All Tournament Team | Bobby Pentino | Lyndsey Roofing Softball | NIT - USSSA - Points | Juno Athletics NIT | 2021 |
|
| All Tournament Team | Brandyn Ladetto | Deeply Kneaded/Thunder Gun Express | NIT - USSSA - Points | OSS Apparel D NIT | 2024 |
|
| All Tournament Team | Andrew Leandre | Woo City Wolf Pack | NIT - USSSA - Points | Wishes Candle D NIT | 2024 |
|
| All Tournament Team | Bobby Pentino | L.A.S. | NIT - USSSA - Points | Jimmy Dogs Memorial NIT - D | 2024 |
|
| All Tournament Team | Brandyn Ladetto | Ellis Painting | NIT - USSSA - Points | Wishes Candle D NIT | 2025 |
|
| All Tournament Team | Bobby Pentino | Reapers/LAS | NIT - USSSA - Points | Jimmy Dogs Memorial NIT - D | 2025 |
|
| All Tournament Team | Brandyn Ladetto | Miller's Homeport/ TopTier/ First D | State - USSSA | Massachusetts D State Tournament | 2012 |
|
| All Tournament Team | Chris Bishop | Globe Cleaners/ N.E.Carpet/ USSSA | State - USSSA | Connecticut Mens D States | 2013 |
| All Tournament Team | Bobby Pentino | Just Bring It | State - USSSA | Connecticut Mens D States | 2013 |
|
| All Tournament Team | Richard Countryman | RDD/ Chicago Sam's/ Walk Off Sports | State - USSSA | CT Mens D States | 2015 |
|
| All Tournament Team | Richard Countryman | Globo Gym/Shark Sports | State - USSSA | Mens D States RESCHEDULED | 2017 |
| All Tournament Team | Bobby Pentino | Globo Gym/Shark Sports | State - USSSA | Mens D States RESCHEDULED | 2017 |
| All Tournament Team | Michael Wills | Globo Gym/Shark Sports | State - USSSA | Mens D States RESCHEDULED | 2017 |
|
| Tournament MVP | stephen Bailey | RDD/SheGone/RIOT | State - USSSA | CT Mens D States | 2020 |
|
| Tournament MVP | stephen Bailey | RDD/Webby/RIOT | State - USSSA | Mens D State Tournament | 2021 |
| All Tournament Team | Brandyn Ladetto | RDD/Webby/RIOT | State - USSSA | Mens D State Tournament | 2021 |
|
| All Tournament Team | Andrew Leandre | Full Send/Fades Away/OSS Apparel | State - USSSA | Mass Men's D State Tournament | 2021 |
|
| All Tournament Team | Matt Angelillo | Whalers/BYB/Marlin Roofing | State - USSSA | Mens D State Tournament | 2023 |
| All Tournament Team | Matt Angelillo | Whalers/BYB/Marlin Roofing | State - USSSA | Mens D State Tournament | 2023 |
|
| All Tournament Team | Luis Lopez | L.A.S. | State - USSSA | Mens D State Tournament | 2024 |
| All Tournament Team | Bobby Pentino | L.A.S. | State - USSSA | Mens D State Tournament | 2024 |
|
| All Tournament Team | Brandyn Ladetto | Ellis Painting | State - USSSA | Men's D State Tournament | 2025 |
|
| All Tournament Team | Bobby Pentino | Reapers/LAS | State - USSSA | Mens D State Tournament | 2025 |
|
| All Tournament Team | Luis Lopez | 6th Boro / Falcone Consulting FCES | State - GSL | ORANGE HAMMER GSL D STATES | 2019 |
| All Tournament Team | Luis Lopez | 6th Boro / Falcone Consulting FCES | State - GSL | ORANGE HAMMER GSL D STATES | 2019 |
|
| Defensive Tournament MVP | Bobby Pentino | L.A.S. | State - GSL | Mens GSL D/E States | 2023 |
| All Tournament Team | Luis Lopez | L.A.S. | State - GSL | Mens GSL D/E States | 2023 |
|
| All Tournament Team | Bobby Pentino | Country Tavern/Chicago Sams | State Level 2 - USSSA | Beast of the East | 2014 |
|
| All Tournament Team | Joe Guardia | mckay's/union brewhouse | State Level 2 - USSSA | Spring States | 2016 |
|
| All Tournament Team | Andrew Leandre | E.M.B | State Level 2 - USSSA | Lil Firecracker | 2020 |
|
| All Tournament Team | Chris Bishop | KL&R Construction/Country Paint Wor | Regional - USSSA | NE Mens D National | 2010 |
|
| All Tournament Team | Richard Countryman | RDD/ Chicago Sam's/ Walk Off Sports | Regional - USSSA | Mens Northeast D National | 2015 |
|
| All Tournament Team | stephen Bailey | MJV/HEO sports | Regional - USSSA | USSSA Men's National | 2019 |
|
| All Tournament Team | stephen Bailey | RDD/Webby/RIOT | Regional - USSSA | Mens D Northeast National | 2021 |
| All Tournament Team | Luis Lopez | The 6th Boro / FCES | Regional - USSSA | Mens D Northeast National | 2021 |
|
| All Tournament Team | Joe Guardia | Energy Monster/TDC Energy | World - USSSA | USSSA Men's D Slow Pitch World Tournament | 2017 |
|
| All Tournament Team | Michael Wills | Carbombs | Qualifier - USSSA - Points | Sunfest | 2012 |
|
| All Tournament Team | Brandyn Ladetto | First degree/millers/top tier | NIT - USSSA - Berth | Reebok Sports E NIT #2 | 2012 |
|
| All Tournament Team | Joe Guardia | Arc Angels Softball/Energy Monster | NIT - USSSA - Berth | Easton Sports "E" NIT | 2013 |
|
| All Tournament Team | Joe Guardia | mckay's softball/british beer compa | NIT - USSSA - Berth | ELMWOOD SPORTS MENS E NIT | 2015 |
|
| All Tournament Team | Michael Fesko | Twistedsports.net/Mashers | NIT - USSSA - Berth | 2 Guys Sports Solutions E NIT | 2017 |
|
| All Tournament Team | Michael Fesko | Twistedsports.net/Mashers | State - USSSA | Mens E States | 2017 |
|
| Tournament MVP | Adam Bisson | George's Pizza | State - USSSA | Rhode Island Men's E States | 2017 |
|
| All Tournament Team | Joe Guardia | Fades Away Barbershop | State Level 2 - USSSA | 7th Annual Easton Mixed Firecracker | 2022 |
| All Tournament Team | Joe Guardia | Renegades/NE Tower Service | State Level 2 - USSSA | 7th Annual Easton Mixed Firecracker | 2022 |
| All Tournament Team | Bobby Pentino | Stamford Coed/RockBottom/Win4Butch | State Level 2 - USSSA | 7th Annual Easton Mixed Firecracker | 2022 |
|
| Defensive Tournament MVP | Joe Guardia | Tuna Shots/C.U.Next Tourney/4TF | State Level 2 - USSSA | Easton Mixed Firecracker - 9th Annual | 2024 |
|
| All Tournament Team | Bobby Pentino | Smash It Sports Coed | Qualifier - USSSA - Points | Beach Bash Mixed Series #1 | 2018 |
|
| All Tournament Manager | Bobby Pentino | Stamford Coed/Robeks/OSS | Qualifier - USSSA - Points | CT GSL Mixed Open States | 2019 |
| All Tournament Manager | Bobby Pentino | Stamford Coed/Robeks/OSS | Qualifier - USSSA - Points | CT GSL Mixed Open States | 2019 |
|
| All Tournament Manager | Bobby Pentino | Stamford Coed/OSS Apparel | Qualifier - USSSA - Points | Mixed Sunday Funday | 2020 |
| All Tournament Manager | Bobby Pentino | OSS COED/6th Boro/SC | Qualifier - USSSA - Points | Mixed Sunday Funday | 2020 |
|
| All Tournament Manager | Bobby Pentino | Stamford Coed/OSS Apparel | Qualifier - USSSA - Points | Mixed March Madness | 2020 |
|
| All Tournament Manager | Bobby Pentino | Stamford Coed/OSS Apparel | State Level 2 - USSSA | Mixed USSSA Open States | 2020 |
|
| All Tournament Team | Bobby Pentino | Stamford Coed/Win4Butch | Qualifier - USSSA - Points | Mixed Cinco De Mayo Bash | 2025 |
|
| All Tournament Team | Bobby Pentino | Stamford Coed/Win4Butch | Qualifier - USSSA - Points | Mixed Holiday Bash | 2025 |
|
| All Tournament Team | Matt Angelillo | Varsity Blues | State - GSL | GSL Coed State | 2025 |
|
| All Tournament Team | Richard Countryman | Stamford Coed/Robeks/OSS | State Level 2 - USSSA | 2019 USSSA Winter Worlds - E, Rec E, Wm D, Coed Up | 2019 |
| All Tournament Team | Richard Countryman | Stamford Coed/Robeks/OSS | State Level 2 - USSSA | 2019 USSSA Winter Worlds - E, Rec E, Wm D, Coed Up | 2019 |
| All Tournament Team | Bobby Pentino | Stamford Coed/Robeks/OSS | State Level 2 - USSSA | 2019 USSSA Winter Worlds - E, Rec E, Wm D, Coed Up | 2019 |
| All Tournament Team | Bobby Pentino | Stamford Coed/Robeks/OSS | State Level 2 - USSSA | 2019 USSSA Winter Worlds - E, Rec E, Wm D, Coed Up | 2019 |
|
| All Tournament Team | Bobby Pentino | 6B/Stamford/Win4Butch | World - USSSA SpecialtyProgram | USSSA Mixed World Tournament | 2022 |
|
| All Tournament Team | Michael Komendowski | Stamford Coed/Win4Butch | World - USSSA | USSSA Mixed World Tournament | 2021 |
| All Tournament Team | Bobby Pentino | Stamford Coed/Win4Butch | World - USSSA | USSSA Mixed World Tournament | 2021 |
|
| All Tournament Team | Brandyn Ladetto | Dirty Birds | Qualifier - USSSA - Points | Holyoke Mixed D | 2013 |
|
| All Tournament Team | Brandyn Ladetto | Dirty Birds/ATWLD | Qualifier - USSSA - Points | Max Cap Team Tourney | 2014 |
|
| All Tournament Team | Michael Komendowski | DUB/Mr.Ed’sPainting/ProAmToolRental | Qualifier - USSSA - Points | Mixed Beach Bash | 2021 |
|
| All Tournament Team | Luis Lopez | Stamford Coed/Elite Limo | Qualifier - GSL - Points | 2018 GSL Coed World Tournament | 2018 |
| All Tournament Team | Michael Wills | Stamford Coed/Elite Limo | Qualifier - GSL - Points | 2018 GSL Coed World Tournament | 2018 |
| All Tournament Team | Michael Wills | Stamford Coed/Elite Limo | Qualifier - GSL - Points | 2018 GSL Coed World Tournament | 2018 |
|
| All Tournament Team | Bobby Pentino | Stamford Co-ed | NIT - USSSA - Berth | IDFK Mixed D NIT | 2015 |
|
| Tournament CO-MVP | Brandyn Ladetto | Dirty Birds/ATWLD | State - USSSA | CT USSSA Mixed States | 2014 |
| All Tournament Team | Bobby Pentino | Black & Yellow | State - USSSA | CT USSSA Mixed States | 2014 |
|
| All Tournament Team | Bobby Pentino | Stamford Co-ed | State - USSSA | CT Mixed D State Tournament | 2015 |
|
| All Tournament Team | Brandyn Ladetto | Get Some/The Well | State - USSSA | CT Mixed D States | 2016 |
| All Tournament Team | Bobby Pentino | Stamford Coed/Walkoff Sports | State - USSSA | CT Mixed D States | 2016 |
| All Tournament Team | Felipe Rivera | Scared Hitless | State - USSSA | CT Mixed D States | 2016 |
|
| All Tournament Team | Luis Lopez | Stamford Coed/Elite Limo | State - USSSA | CT Mixed D States | 2018 |
| All Tournament Team | Bobby Pentino | Stamford Coed/Elite Limo | State - USSSA | CT Mixed D States | 2018 |
|
| Defensive Tournament MVP | Michael Komendowski | DUB/Mr.Ed’sPainting/ProAmToolRental | State - USSSA | Mixed D/E State Tournament | 2021 |
|
| All Tournament Team | Joe Guardia | Renegades/NE Tower Service | State - USSSA | Mixed D State Tournament | 2022 |
|
| All Tournament Team | Matt Angelillo | Varsity Blues | State - USSSA | CT Mixed D & E States | 2025 |
|
| All Tournament Team | Brandyn Ladetto | Get Some/The Well | Regional - USSSA | Mixed Northeast D National | 2016 |
|
| All Tournament Team | Luis Lopez | Six Boro | Regional - USSSA | Mixed Northeast D National | 2019 |
|
| All Tournament Team | stephen Bailey | Stamford Coed/Robeks | World - USSSA | USSSA Mixed World Tournament East | 2017 |
|
| All Tournament Team | Matt Angelillo | Rugrats/Allstate/Evo9x | Qualifier - USSSA - Points | Yatzee Ink Season Kickoff Open D | 2016 |
| All Tournament Team | Brandyn Ladetto | Rugrats/Allstate/Evo9x | Qualifier - USSSA - Points | Yatzee Ink Season Kickoff Open D | 2016 |
|
| Tournament CO-MVP | Chris Bishop | Globe Cleaners/ N.E.Carpet/ USSSA | NIT - USSSA - Berth | Easton Sports Open NIT | 2013 |
|
| All Tournament Team | Chris Bishop | Globe Cleaners | NIT - USSSA - Berth | Reebok Open NIT | 2014 |
|
| All Tournament Team | Brandyn Ladetto | Aftermath Softball | NIT - USSSA - Berth | 5th Annual Andy Beloli Open NIT | 2019 |
| All Tournament Team | Brandyn Ladetto | Aftermath Softball | NIT - USSSA - Berth | 5th Annual Andy Beloli Open NIT | 2019 |
| All Tournament Team | Michael McGonigle | Aftermath Softball | NIT - USSSA - Berth | 5th Annual Andy Beloli Open NIT | 2019 |
| All Tournament Team | Michael McGonigle | Aftermath Softball | NIT - USSSA - Berth | 5th Annual Andy Beloli Open NIT | 2019 |