| Date | Match | Location | Time / Result |
|
| 09/13/08 | Cornell Fall Open | Ithaca, N.Y. | All Day |
| | Laser South #1 | Annapolis, Md. | All Day |
| | Old Dominion BYO Women & Men Radial | Norfolk, Va. | All Day |
| | Riley Cup | Norfolk, Va. | All Day |
| 09/14/08 | Cornell Fall Open | Ithaca, N.Y. | ALL DAY |
| | Laser South #1 | Annapolis, Md. | ALL DAY |
| | Old Dominion BYO Women & Men Radial | Norfolk, Va. | ALL DAY |
| | Riley Cup | Norfolk, Va. | ALL DAY |
| 09/20/08 | Central Fall #1 | Toms River, N.J. | All Day |
| | Hatch Brown Regatta | Boston, Mass. | ALL DAY |
| | Nevins Trophy | Kings Point, N.Y. | All Day |
| | New York Maritime Fall Open | Throggs Neck, N.Y. | All Day |
| 09/21/08 | Central Fall #1 | Toms River, N.J. | ALL DAY |
| | Hatch Brown Regatta | Boston, Mass. | ALL DAY |
| | Nevins Trophy | Kings Point, N.Y. | ALL DAY |
| | New York Maritime Fall Open | Throggs Neck, N.Y. | ALL DAY |
| 09/27/08 | Faye Bennet / MAISA Women's Singlehandeds | Annapolis, Md. | All Day |
| | Laser South #2 | Annapolis, Md. | All Day |
| | North Fall #1 | Geneva, N.Y. | All Day |
| | SMC Open For the Senators Cup | St. Mary's City, Md. | All Day |
| 09/28/08 | Faye Bennet / MAISA Women's Singlehandeds | Annapolis, Md. | ALL DAY |
| | Laser South #2 | Annapolis, Md. | ALL DAY |
| | North Fall #1 | Geneva, N.Y. | ALL DAY |
| | SMC Open For the Senators Cup | St. Mary's City, Md. | ALL DAY |
| 10/04/08 | Navy Team Race Open | Annapolis, Md. | All Day |
| | South Fall #2 / Tom Curtis Regatta | Washington, D.C. | All Day |
| 10/05/08 | Navy Team Race Open | Annapolis, Md. | ALL DAY |
| | South Fall #2 / Tom Curtis Regatta | Washington, D.C. | ALL DAY |
| | Hap Moore Team Race | New Haven, Conn. | All Day |
| 10/11/08 | HWS Fall Intersectional | Geneva, N.Y. | 1st / 18 Teams |
| | MAISA Men's Singlehandeds / Carl Van Duyne Trophy | Kings Point, N.Y. | All Day |
| | Navy Fall Women's Intersectional | Annapolis, Md. | All Day |
| | Hap Moore Team Race | New Haven, Conn. | ALL DAY |
| 10/12/08 | HWS Fall Intersectional | Geneva, N.Y. | ALL DAY |
| | MAISA Men's Singlehandeds / Carl Van Duyne Trophy | Kings Point, N.Y. | ALL DAY |
| | Navy Fall Women's Intersectional | Annapolis, Md. | ALL DAY |
| 10/18/08 | Central Fall #2 | Chestertown, Md. | All Day |
| | Navy Fall Intersectional | Annapolis, Md. | All Day |
| | North Fall #2 | Throggs Neck, N.Y. | All Day |
| 10/19/08 | Central Fall #2 | Chestertown, Md. | ALL DAY |
| | Navy Fall Intersectional | Annapolis, Md. | ALL DAY |
| | North Fall #2 | Throggs Neck, N.Y. | ALL DAY |
| 10/24/08 | ICSA Men's Singlehandeds | Ithaca, N.Y. | All Day |
| | ICSA Women's Singlehandeds | Ithaca, N.Y. | All Day |
| 10/25/08 | Hoyt Trophy | Providence, R.I. | All Day |
| | ICSA Men's Singlehandeds | Ithaca, N.Y. | ALL DAY |
| | ICSA Women's Singlehandeds | Ithaca, N.Y. | ALL DAY |
| | Kings Point Dinghy Open | Kings Point, N.Y. | All Day |
| | MAISA Fall Open | Norfolk, Va. | All Day |
| | Stu Nelson (Women's) | New London, Conn. | All Day |
| 10/26/08 | Hoyt Trophy | Providence, R.I. | ALL DAY |
| | ICSA Men's Singlehandeds | Ithaca, N.Y. | ALL DAY |
| | ICSA Women's Singlehandeds | Ithaca, N.Y. | ALL DAY |
| | Kings Point Dinghy Open | Kings Point, N.Y. | ALL DAY |
| | MAISA Fall Open | Norfolk, Va. | ALL DAY |
| | Stu Nelson (Women's) | New London, Conn. | ALL DAY |
| 11/01/08 | Schell Trophy | Boston, Mass. | All Day |
| | War Memorial Regatta | Ithaca, N.Y. | All Day |
| 11/02/08 | Schell Trophy | Boston, Mass. | ALL DAY |
| | War Memorial Regatta | Ithaca, N.Y. | ALL DAY |
| 11/08/08 | MAISA Sloops | Kings Point, N.Y. | All Day |
| | MAISA Women's Fall Dinghy | Annapolis, Md. | All Day |
| 11/09/08 | MAISA Sloops | Kings Point, N.Y. | ALL DAY |
| | MAISA Women's Fall Dinghy | Annapolis, Md. | ALL DAY |
| 11/15/08 | Atlantic Coast Dinghies | Geneva, N.Y. | All Day |
| | Atlantic Coast Women | Washington, D.C. | All Day |
| 11/16/08 | Atlantic Coast Dinghies | Geneva, N.Y. | ALL DAY |
| | Atlantic Coast Women | Washington, D.C. | ALL DAY |
| 11/21/08 | ICSA Sloops / Cornelius Shields Trophy | Tampa, Fla. | All Day |
| 11/22/08 | ICSA Sloops / Cornelius Shields Trophy | Tampa, Fla. | ALL DAY |
| 11/23/08 | ICSA Sloops / Cornelius Shields Trophy | Tampa, Fla. | ALL DAY |
| 01/03/09 | Rose Bowl Regatta | Los Angeles, Calif. | All Day |
| 01/04/09 | Rose Bowl Regatta | Los Angeles, Calif. | ALL DAY |
| 02/14/09 | Mendelblatt Team Race | Tampa, Fla. | All Day |
| 02/15/09 | Mendelblatt Team Race | Tampa, Fla. | All Day |
| 02/21/09 | College of Charleston Spring Intersectional | Charleston, S.C. | All Day |
| | USF Women's Intersectional | Tampa, Fla. | All Day |
| 02/22/09 | College of Charleston Spring Intersectional | Charleston, S.C. | All Day |
| | USF Women's Intersectional | Tampa, Fla. | All Day |
| 02/28/09 | Bob Bavier Team Race | Charleston, S.C. | All Day |
| | The Tom Noble Team Race | Chestertown, Md. | All Day |
| 03/01/09 | Bob Bavier Team Race | Charleston, S.C. | All Day |
| | The Tom Noble Team Race | Chestertown, Md. | All Day |
| 03/07/09 | Charleston Women's | Charleston, S.C. | All Day |
| | John Jackson / Graham Hall Memorial Team Race | Annapolis, Md. | All Day |
| | ODU Spring Open | Norfolk, Va. | All Day |
| 03/08/09 | Charleston Women's | Charleston, S.C. | All Day |
| | John Jackson / Graham Hall Memorial Team Race | Washington, D.C. | All Day |
| | ODU Spring Open | Norfolk, Va. | All Day |
| 03/14/09 | Navy Spring Women's Intersectional | Annapolis, Md. | All Day |
| | St. Mary's Team Race Intersectional | St. Mary's City, Md. | All Day |
| 03/15/09 | Navy Spring Women's Intersectional | Annapolis, Md. | All Day |
| | St. Mary's Team Race Intersectional | St. Mary's City, Md. | All Day |
| 03/21/09 | St. Mary's Women's Intersectional | St. Mary's City, Md. | All Day |
| | Truxtun Umsted | Annapolis, Md. | All Day |
| 03/22/09 | St. Mary's Women's Intersectional | St. Mary's City, Md. | All Day |
| | Truxtun Umsted | Annapolis, Md. | All Day |
| 03/28/09 | Aarigan Memorial | Washington, D.C. | All Day |
| | Aaron Szambecki Team Race Intersectional | Norfolk, Va. | All Day |
| | Boston Dinghy Cup | Cambridge, Mass. | All Day |
| | Old Guard for Mosbacher | Kings Point, N.Y. | All Day |
| 03/29/09 | Aarigan Memorial | Washington, D.C. | All Day |
| | Aaron Szambecki Team Race Intersectional | Norfolk, Va. | All Day |
| | Boston Dinghy Cup | Cambridge, Mass. | All Day |
| | Old Guard for Mosbacher | Kings Point, N.Y. | All Day |
| 04/04/09 | Southern New England Team Race | New London, Conn. | All Day |
| | Women's Dellenbaugh Trophy | Providence, R.I. | All Day |
| 04/05/09 | Southern New England Team Race | New London, Conn. | All Day |
| | Women's Dellenbaugh Trophy | Providence, R.I. | All Day |
| 04/11/09 | MAISA Team Race / Capt. Prosser Trophy | Annapolis, Md. | All Day |
| 04/12/09 | MAISA Team Race / Capt. Prosser Trophy | Annapolis, Md. | All Day |
| 04/18/09 | America Trophy | Throggs Neck, N.Y. | All Day |
| | MAISA Spring Open | Ithaca, N.Y. | All Day |
| 04/19/09 | America Trophy | Throggs Neck, N.Y. | All Day |
| | MAISA Spring Open | Ithaca, N.Y. | All Day |
| | Women's Dublin Trophy | Medford, Mass. | All Day |
| 04/25/09 | Admiral's Cup | Kings Point, N.Y. | All Day |
| | MAISA Women's Spring Dinghy | Geneva, N.Y. | All Day |
| | Thompson Trophy | New London, Conn. | All Day |
| 04/26/09 | Admiral's Cup | Kings Point, N.Y. | All Day |
| | MAISA Women's Spring Dinghy | Geneva, N.Y. | All Day |
| | Thompson Trophy | New London, Conn. | All Day |
| 05/02/09 | ICSA Eastern Semi-Finals | TBA | All Day |
| | ICSA Western Semi-Finals | Minneapolis, Minn. | All Day |
| 05/03/09 | ICSA Eastern Semi-Finals | TBA | All Day |
| | ICSA Western Semi-Finals | Minneapolis, Minn. | All Day |
| 05/25/09 | ICSA Women's Gerald Miller Trophy | Palo Alto, Calif. | All Day |
| 05/26/09 | ICSA Women's Gerald Miller Trophy | Palo Alto, Calif. | All Day |
| 05/27/09 | ICSA Women's Gerald Miller Trophy | Palo Alto, Calif. | All Day |
| 05/29/09 | ICSA Team Race / Walter Wood Trophy | Berkeley, Calif. | All Day |
| 05/30/09 | ICSA Team Race / Walter Wood Trophy | Berkeley, Calif. | All Day |
| 05/31/09 | ICSA Team Race / Walter Wood Trophy | Berkeley, Calif. | All Day |
| 06/01/09 | ICSA Dinghy National Championship | Palo Alto, Calif. | All Day |
| 06/02/09 | ICSA Dinghy National Championship | Palo Alto, Calif. | All Day |
| 06/03/09 | ICSA Dinghy National Championship | Palo Alto, Calif. | All Day |