| ISSA Singlehanded Champs - Radial | Sehome | National Championship | Singlehanded | | Official | 7/18 |
| Fort Monroe Scrimmage II | Hampton | In-League | 2 Divisions | | Official | 2/12 |
| MASSA 2014 Fall Fleet Championship | Sailing Center Chesapeake | District Championship | 2 Divisions | | Official | 12/18 |
| Fort Monroe Scrimmage | YSV Fort Monroe | In-League | 2 Divisions | | Official | 10/14 |
| Fort Monroe Scrimmage JV | Hampton | In-League | 1 Division | | Official | 8/8 |
| HCS/HRA Fleet Race Regatta | Hampton | In-District | 2 Divisions | | Official | 9,19/19 |
| HCS/HRA Fleet Race Regatta JV | HCS/HRA | In-District | 1 Division | | Official | 6/8 |
| VISA NCS Fleet Race Regatta | Norfolk Collegiate School | In-District | 2 Divisions | | Official | 4,14,22/24 |
| VISA NCS Fleet Race Regatta JV | Hampton | In-District | 1 Division | | Official | 7/8 |
| VISA Poquoson Fleet Race Regatta | Hampton | In-District | 2 Divisions | | Pending | 3/18 |
| VISA Poq. Fleet Race Regatta JV | Hampton | In-District | 1 Division | | Official | 4/12 |
| VISA NA Silver Team Race (2v2) | Norfolk Academy | In-District | Team | | Official | 2/9 |
| Massa Cressy Qualifier - Radial | The WaterFront Center | District Championship | Singlehanded | | Official | 1/37 |
| VISA CCS Fleet Regatta | Christchurch school | In-District | 2 Divisions | | Official | 6,14/18 |
| VISA CCS Fleet Regatta JV | Hampton | In-District | 1 Division | | Official | 9/11 |