| Date | Event | Time |
| Nov 4 2008 - Tue | Board of Directors Meeting (Room C-112 HKHS) | 7:00 pm |
| Dec 2 2008 - Tue | Board of Directors Meeting (Room C-112 HKHS) | 7:00 p.m. |
| Dec 7 2008 - Sun | League Adult Christmas Party (Location: TBA) | 6:00 p.m. |
| Jan 6 2009 - Tue | Annual Meeting/Board of Directors Meeting | 7:30 p.m. |
| Jan 20 2009 - Tue | Registration – Haddam Fire House (7:00 p.m. – 9:00 p.m.) | 7:00 p.m. |
| Jan 22 2009 - Thu | Registration – Haddam Fire House (9:00 a.m. – 12:00 p.m.) | 9:00 a.m. |
| Jan 27 2009 - Tue | Registration – Haddam Fire House (7:00 p.m. – 9:00 p.m.) | 7:00 p.m. |
| Jan 31 2009 - Sat | Registration – Haddam Fire House (9:00 a.m. – 12:00 noon) | 9:00 a.m. |
| Feb 3 2009 - Tue | Board of Directors Meeting (Town Hall Annex - 2nd Floor) | 7:00 p.m. |
| Mar 1 2009 - Sun | Deadline for Junior Baseball & Softball Election (12 yr olds) | |
| Mar 3 2009 - Tue | Manager/Coaches Orientation Meeting | 6:00 p.m. |
| Mar 3 2009 - Tue | Board of Directors Meeting (Town Hall Annex - 2nd Floor) | 7:00 p.m. |
| Mar 14 2009 - Sat | Baseball/Softball Skills Evaluation – HKHS Field House | TBA |
| Mar 15 2009 - Sun | Major League Baseball Draft | 1:00 p.m. |
| Mar 15 2009 - Sun | Major League Softball Draft | 7:00 p.m. |
| Mar 16 2009 - Mon | Major League Practice Begins | |
| Mar 23 2009 - Mon | Minor League Baseball Draft | 7:00 p.m. |
| Mar 23 2009 - Mon | Minor League Softball Draft | 7:00 p.m. |
| Mar 24 2009 - Tue | Minor League Practice Begins | |
| Mar 29 2009 - Sun | Managers/Coaches Clinic (Tentative) | |
| Apr 7 2009 - Tue | Board of Directors Meeting (Town Hall Annex - 2nd Floor) | 7:00 p.m. |
| Apr 8 2009 - Wed | League Directors & Managers/Coaches Meeting | 7:00 p.m. |
| Apr 18 2009 - Sat | Major & Minor League Baseball Opening Day | |
| Apr 19 2009 - Sun | Major & Minor League Softball Opening Day | |
| Apr 25 2009 - Sat | Instructional Baseball and Softball and T-Ball Opening Day | |
| Apr 26 2009 - Sun | Rain Date for Opening Day(s) | |
| May 5 2009 - Tue | Board of Directors Meeting (Town Hall Annex - 2nd Floor) | 7:00 p.m. |
| May 16 2009 - Sat | Jay Benedict Memorial Baseball Tournament | TBA |
| May 16 2009 - Sat | New Britain Rock Cats “Hit, Run & Throw” Competition | TBA |
| May 17 2009 - Sun | Jay Benedict Memorial Baseball Tournament Rain Date | |
| May 25 2009 - Mon | Town of Haddam Memorial Day Parade | TBA |
| Jun 2 2009 - Tue | Board of Directors Meeting (Town Hall Annex - 2nd Floor) | 7:00 p.m. |
| Jun 11 2009 - Thu | Managers Meeting – Selection of Tournament Teams | TBA |
| Jun 13 2009 - Sat | New Britain Rock Cats Family Night | TBA |
| Jun 15 2009 - Mon | Birth Certificates Due for Tournament Teams | |
| Jun 19 2009 - Fri | Last Day of Regular Season | |
| Jul 7 2009 - Tue | Board of Directors Meeting @ GHAC | 7:00 p.m. |
| Aug 4 2009 - Tue | Board of Directors Meeting (Town Hall Annex - 2nd Floor) | 7:00 p.m. |
| Sep 1 2009 - Tue | Board of Directors Meeting (Town Hall Annex - 2nd Floor) | 7:00 p.m. |
| Sep 11 2009 - Fri | Haddam River Days | |
| Sep 12 2009 - Sat | Haddam River Days | |
| Oct 6 2009 - Tue | Board of Directors Meeting (Town Hall Annex - 2nd Floor) | 7:00 p.m. |
| Nov 3 2009 - Tue | Board of Directors Meeting (Town Hall Annex - 2nd Floor) | 7:00 p.m. |
| Dec 1 2009 - Tue | Board of Directors Meeting (Town Hall Annex - 2nd Floor) | 7:00 p.m. |
| Jan 5 2010 - Tue | Annual Meeting/Board of Directors Meeting | 7:00 p.m. |