| Date | Away Team | Home Team | Field | |
| Wed 10/1/2008 | Middletown | Bristol | Bristol | |
| Wed 10/1/2008 | CSP | West Hartford | West Hartford | |
| Wed 10/8/2008 | West Hartford | New Britain | New Britain | |
| Wed 10/8/2008 | Bristol | CSP | CSP | |
| Wed 10/15/2008 | Middletown | West Hartford | West Hartford | |
| Wed 10/15/2008 | New Britain | CSP | CSP | |
| Wed 10/22/2008 | Bristol | West Hartford | West Hartford | |
| Wed 10/22/2008 | New Britain | Middletown | Middletown | |
| Wed 10/29/2008 | Middletown | CSP | CSP | |
| Wed 10/29/2008 | New Britain | Bristol | Bristol | |
| Wed 11/5/2008 | Bristol | Middletown | BRISTOL | |
| Wed 11/5/2008 | West Hartford | CSP | CSP | |
| Wed 11/12/2008 | New Britain | West Hartford | West Hartford | |
| Wed 11/12/2008 | CSP | Bristol | Bristol | |
| Wed 11/19/2008 | Middletown | West Hartford | West Hartford | |
| Wed 11/19/2008 | CSP | New Britain | New Britain | |
| NO MATCH 11/26/08 HAPPY THANKSGIVING | ||||
| Wed 12/3/2008 | West Hartford | Bristol | Bristol | |
| Wed 12/3/2008 | Middletown | New Britain | New Britain | |
| Wed 12/10/2008 | CSP | Middletown | Middletown | |
| Wed 12/10/2008 | Bristol | New Britain | New Britain | |
| Wed 12/17/2008 | Middletown | Bristol | Bristol | |
| Wed 12/17/2008 | CSP | West Hartford | West Hartford | |
| NO MATCH 12/24/08 & NO MATCH 12/31/08 | ||||
| Wed 1/7/2009 | West Hartford | New Britain | New Britain | |
| Wed 1/7/2009 | Bristol | CSP | CSP | |
| Wed 1/14/2009 | West Hartford | Middletown | WEST HARTFORD | |
| Wed 1/14/2009 | New Britain | CSP | CSP | |
| Wed 1/21/2009 | Bristol | West Hartford | West Hartford | |
| Wed 1/21/2009 | Middletown | New Britain | New Britain | |
| SECOND HALF BEGINS | ||||
| Wed 1/28/2009 | Middletown | CSP | CSP | |
| Wed 1/28/2009 | New Britain | Bristol | Bristol | |
| Wed 2/4/2009 | Bristol | Middletown | Middletown | |
| Wed 2/4/2009 | West Hartford | CSP | CSP | |
| Wed 2/11/2009 | New Britain | West Hartford | West Hartford | |
| Wed 2/11/2009 | CSP | Bristol | Bristol | |
| Wed 2/18/2009 | Middletown | West Hartford | West Hartford | |
| Wed 2/18/2009 | CSP | New Britain | New Britain | |
| Wed 2/25/2009 | West Hartford | Bristol | Bristol | |
| Wed 2/25/2009 | New Britain | Middletown | Middletown | |
| Wed 3/4/2009 | Middletown | CSP | CSP | |
| Wed 3/4/2009 | Bristol | New Britain | New Britain | |
| Wed 3/11/2009 | Middletown | Bristol | Bristol | |
| Wed 3/11/2009 | CSP | West Hartford | West Hartford | |
| Wed 3/18/2009 | West Hartford | New Britain | New Britain | |
| Wed 3/18/2009 | Bristol | CSP | CSP | |
| Wed 3/25/2009 | West Hartford | Middletown | Middletown | |
| Wed 3/25/2009 | New Britain | CSP | CSP | |
| Wed 4/1/2009 | Bristol | West Hartford | West Hartford | |
| Wed 4/1/2009 | Middletown | New Britain | New Britain | |
| Wed 4/8/2009 | CSP | Middletown | Middletown | |
| Wed 4/8/2009 | New Britain | Bristol | Bristol | |
| Wed 4/15/2009 | Bristol | Middletown | Middletown | |
| Wed 4/15/2009 | West Hartford | CSP | CSP | |
| Wed 4/22/2009 | New Britain | West Hartford | West Hartford | |
| Wed 4/22/2009 | CSP | Bristol | Bristol | |
| Wed 4/29/2009 | West Hartford | Middletown | Middletown | |
| Wed 4/29/2009 | CSP | New Britain | New Britain | |
| BANQUET 05/06/09 | ||||