| April | |
| Apr 2 | HYC Wednesdays begin | HYC |
| Apr 5 | OPCYC Saturdays begin | OPCYC |
| Apr 9 | Little Creek Wednesdays begin | BBSA |
| Apr 10 | Willoughby Thursdays begin | BBSA - Willoughby |
| Apr 13 | CCV Tune-Up Race | CCV |
| Apr 18 | Barnacle Fridays begin | PBC |
| Apr 19 | Azalea Festival Regatta - NEW! | NNSA |
| Apr 20 | Spring Series #1 & #2 (401/402) | CCV |
| Apr 23 | York River Wednesdays begin | YRYC |
| Apr 27 | Spring Series #3 (403) | CCV |
| May | |
| May 4 | Spring Series #5 & #6 (403/404) | CCV |
| May 17 | Cape Henry Cup (405) | BBSA |
| May 18 | Spring J/24 Day (406) | HYC |
| May 30 | Southern Bay Race Week - Opening and Registration | HYC-OPCYC-CCV |
| May 30 | Southern Bay Race Week - Racing (407) | HYC-OPCYC-CCV |
| May 31 | Southern Bay Race Week - Racing (408) | HYC-OPCYC-CCV |
| June | |
| June 1 | Southern Bay Race Week - Racing (409) | HYC-OPCYC-CCV |
| June 7 | Harborfest Hometowne Regatta (410)
| PBC |
| June 7 | York River Cup (411) | YRYC |
| June 14 | Hampton Roads Hospice Regatta (412) | HYC |
| June 21 | Cock Island Race | Portsmouth-PBC |
| June 28 | Hanbury Cup | CNUSF |
| July | |
| July 12 | Veteran's Cup (413) | LYC |
| July 11-13 | So. Ches. Bay Leukemia Regatta (445/446) | FBYC |
| July 19 | Little Bay Challenge | BBSA - Willoughby Racers |
| July 19 | Screwpile Lighthouse Challenge - Opening and Registration | SMSA |
| July 20 | Screwpile Lighthouse Challenge - Racing (334) | SMSA |
| July 21 | Screwpile Lighthouse Challenge - Racing (335) | SMSA |
| July 22 | Screwpile Lighthouse Challenge - Racing (336) | SMSA |
| July 26 | Moonlight Triangle (414) | CCV |
| August | |
| Aug 2 | Little Creek Cup (415) | BBSA |
| Aug 9 | Tom Brady Masters Race | HYC |
| Aug 9 | Admirals Cup (416) | YRYC-SYC |
| Aug 10 | Founders Race (417) | CCV |
| Aug 15 | Plantation Light Race (418) | HYC |
| Aug 23-24 | Cape Charles Cup (419/420) | BBSA |
| Aug 30 | Dink Vail-Labor Day Regatta (421) | NY&CC |
| Aug 30-31 | Stingray Point Regatta (448/449) | FBYC |
| Aug 30 - Sep 1 | Annapolis Race Week (501/502/503) | CBYRA |
| September | |
| Sep 6 | Annual Regatta (422) | HYC |
| Sep 13 | Tri-Services Regatta (NNSA host) | OPCYC-LYC-NNSA |
| Sep 14 | Fall Series Races #1 & #2 (423/424) | CCV |
| Sep 21 | Fall Series Races #3(425) | CCV |
| Sep 27 | Neptune's Atlantic Regatta (426) | BBSA |
| Sep 28 | Singlehand Race | HYC |
| October | |
| Oct 4 | Memorial Regatta | BBSA-Willoughby Racers |
| Oct 5 | Fall Series Races #5 & #6 (427/428) | CCV |
| Oct 10-12 | Hospice Turkey Shoot | YPM |
| Oct 25 | 'Round the Lights Race (430) | OPCYC |
| November | |
| Nov 1 | Hot Buttered Rum | BBSA - Willoughby Racers |
| Nov 2 | Frostbite Series #1 | HYC |
| Nov 9 | Frostbite Series #2 | HYC |
| Nov 16 | Frostbite Series #3 | HYC |
| Nov 23 | Frostbite Series #4 | HYC |
| Nov 30 | Frostbite Series #5 | HYC |
| December | |
| Dec 7 | Gaboon Race | HYC |
| January 2009 | |
| Jan 1 | New Year Madness Race | OPCYC-HYC |
| Jan 1 | New Year Day Race | SYC |
