| Year | Sport | Class | Champion | Runnerup | Score | Link |
| 2023 | Volleyball (Boys) | L | Darien | Trumbull | 3-2 (21-25, 25-19, 28-30, 25-21, 15-12) | |
| Volleyball (Boys) | M | Masuk | Cheshire | 3-0 (25-18, 25-19, 25-15) | |
| 2022 | Volleyball (Boys) | L | Darien | Trumbull | 3-0 (25-22, 25-15, 25-10) | |
| Volleyball (Boys) | M | Joel Barlow | New Canaan | 3-0 (25-21, 25-22, 25-20) | |
| 2021 | Volleyball (Boys) | L | Darien | Enfield | 3-1 (18-25, 25-17, 25-22, 25-16) | |
| Volleyball (Boys) | M | Joel Barlow | Newington | 3-1 (25-16, 20-25, 25-17, 25-20) | |
| 2019 | Volleyball (Boys) | L | Staples | Darien | 3-2 (25-22, 25-23, 22-25, 15-25, 17-15) | |
| Volleyball (Boys) | M | Newington | Cheshire | 3-1 (16-25, 25-16, 25-19, 25-22 ) | |
| 2018 | Volleyball (Boys) | L | Staples | Ridgefield | 3-2 (25-16, 26-24, 22-25, 20-25, 15-13) | |
| Volleyball (Boys) | M | Newington | Joel Barlow | 3-2 (26-24, 23-25, 25-22, 22-25, 15-13) | |
| 2017 | Volleyball (Boys) | L | Darien | East Hartford | 3-0 (25-14, 25-19, 25-16) | |
| Volleyball (Boys) | M | Newington | South Windsor | 3-2 (24-26, 20-25, 25-18, 25-15, 16-14) | |
| 2016 | Volleyball (Boys) | L | Ridgefield | Darien | 3-2 (18-25, 25-19, 22-25, 25-22, 15-9) | |
| Volleyball (Boys) | M | South Windsor | Joel Barlow | 3-0 (25-20, 25-22, 25-18) | |
| 2015 | Volleyball (Boys) | L | Ridgefield | Darien | 3-1 (23-25, 25-22, 25-19, 25-18) | |
| Volleyball (Boys) | M | Newington | Joel Barlow | 3-1 (25-21, 20-25, 25-19, 25-19) | |
| 2014 | Volleyball (Boys) | L | Ridgefield | Southington | 3-0 (25-20, 27-25, 25-23) | |
| Volleyball (Boys) | M | Newington | Oxford | 3-0 (25-22, 25-20, 25-20) | |
| 2013 | Volleyball (Boys) | L | Staples | Glastonbury | 3-1 (24-26, 25-17, 25-13, 25-23) | |
| Volleyball (Boys) | M | Oxford | Enfield | 3-0 (25-23, 25-21, 25-20) | |
| 2012 | Volleyball (Boys) | L | Cheshire | Ridgefield | 3-1 (25-20, 25-18, 20-25, 25-21) | |
| Volleyball (Boys) | M | Newington | Oxford | 3-1 (25-20, 18-25, 25-23, 25-17) | |
| 2011 | Volleyball (Boys) | L | Cheshire | Staples | 3-1 (12-25, 25-23, 26-24, 25-22) | |
| Volleyball (Boys) | M | Darien | Newington | 3-2 (23-25, 25-17, 18-25, 25-22, 15-11) | |
| 2010 | Volleyball (Boys) | L | Southington | Staples | 3-2 (10-25, 28-26, 25-23, 19-25, 15-11) | |
| Volleyball (Boys) | M | Lewis Mills | Masuk | 3-1 (19-25 33-31 25-22 26-24) | |
| 2009 | Volleyball (Boys) | L | Staples | Southington | 3-1 (20-25 25-23 25-22 25-15) | |
| Volleyball (Boys) | M | Masuk | Farmington | 3-2 (22-25 25-15 20-25 25-16 15-13) | |
| 2008 | Volleyball (Boys) | L | Staples | Southington | 3-1 (25-14 18-25 25-20 26-24) | |
| Volleyball (Boys) | M | Darien | Enfield | 3-1 (22-25 25-12 25-11 27-25) | |
| 2007 | Volleyball (Boys) | L | Staples | Southington | 3-0 | |
| Volleyball (Boys) | M | Lewis Mills | Enfield | 3-0 | |
| 2006 | Volleyball (Boys) | L | Staples | Newington | 3-0 | |
| Volleyball (Boys) | M | Lewis Mills | Daniel Hand | 3-0 | |
| 2005 | Volleyball (Boys) | L | Shelton | Trumbull | 3-0 | |
| Volleyball (Boys) | M | Maloney | Lewis Mills | 3-0 | |
| 2004 | Volleyball (Boys) | L | Shelton | Ridgefield | 3-1 | |
| Volleyball (Boys) | M | Staples | Lewis Mills | 3-0 | |
| 2003 | Volleyball (Boys) | L | Ridgefield | E.O. Smith | 3-0 | |
| Volleyball (Boys) | M | Staples | Lewis Mills | 3-0 | |
| 2002 | Volleyball (Boys) | L | Glastonbury | Trumbull | 3-1 | |
| Volleyball (Boys) | M | Staples | Lewis Mills | 3-0 | |
| 2001 | Volleyball (Boys) | L | Trumbull | Amity | 3-0 | |
| Volleyball (Boys) | M | Staples | St. Joseph | 3-1 | |