| MASSA Girls Fall Invitational | Georgetown University | National Invitational | 2 Divisions | | Official | 1/16 |
| Atlantic Coast Championship | Archbishop Spalding/Broadneck | National Invitational | 2 Divisions | | Official | 1/18 |
| VISA Fleet Championship | Youth Sailing Virginia | League Championship | 2 Divisions | | Official | 1,2,6/18 |
| VISA JV Fleet Championship | Norfolk Collegiate | League Championship | 1 Division | | Official | 1,2,5,12/14 |
| VISA Christchurch Halloween Race Day | Christchurch School | In-League | 1 Division | | Official | 1,2,3,4,5,6,7,8,9,10,11,12,13,14,15/15 |
| MASSA Fall Invitational | Archbishop Spalding/Broadneck | District Championship | 2 Divisions | | Official | 1/16 |
| VISA Norfolk Academy Fleet Race | Norfolk Yacht and Country Club | In-League | 2 Divisions | | Official | 1,6,7,11/16 |
| VISA York County JV Fleet Race Regatta | Norfolk Yacht and Country Club | In-League | 1 Division | | Official | 11,14,16/17 |
| MASSA Fall Fleet Championship | Youth Sailing Virginia | District Championship | 2 Divisions | | Official | 1/18 |
| VISA Cox, Catholic, PC JV Fleet Regatta | Norfolk Yacht and Country Club | In-League | 1 Division | | Official | 1,6,13/14 |
| VISA Cox, Cath, PC Varsity Fleet Regatta | Catholic HS/Frank W. Cox/Peninsula Catholic | In-League | 2 Divisions | | Official | 1,3,6/16 |
| VISA Christchurch School | Christchurch School | In-League | 1 Division | | Official | 1,2,3,4,5,6,7,8,9,10,11,12,13,14,15/15 |
| MASSA Team Race Championship | Severn Sailing Association | District Championship | Team | | Official | 1/10 |
| VISA Poquoson Fleet Race Regatta | Poquoson | In-League | 2 Divisions | | Official | 2,3,10/15 |
| VISA Christchurch School Team Race | Christchurch School | In-League | Team | | Official | 1,2,3,4/4 |
| VISA Team race Championship | Norfolk Yacht and Country Club | League Championship | Team | | Official | 1,5,7/11 |
| VISA Poquoson JV Fleet Regatta | Youth Sailing Virginia | In-League | 1 Division | | Official | 1,10/13 |
| VISA Christchurch Race Day | Christchurch | In-League | 1 Division | | Official | 1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19/19 |
| VISA HCS Team Race Regatta 2 | Youth Sailing Virginia | In-League | Team | | Official | 1,3,10/13 |
| VISA Christchurch Fleet Regatta | Christchurch | In-League | 2 Divisions | | Official | 1,2,6,7/20 |
| VISA Christchurch JV Fleet Regatta | Christchurch | In-League | 1 Division | | Official | 3,6,7/12 |
| MASSA Cressy Quailifier ILCA 7 | Norfolk Yacht and Country Club | District Champ Qualifier | Singlehanded | | Official | 5/5 |
| MASSA Cressy Quailifier Girls ILCA 6 | Norfolk Yacht and Country Club | District Champ Qualifier | Singlehanded | | Official | 3/7 |
| MASSA Cressy Quailifier Boys ILCA 6 | Norfolk Yacht and Country Club | District Champ Qualifier | Singlehanded | | Official | 3,4,20/20 |
| VISA Hampton City Schools Team Race Regatta | Youth Sailing Virginia | In-League | Team | | Official | 1/7 |
| VISA Maury/Granby Fleet Regatta | Norfolk Yacht and Country Club | In-League | 2 Divisions | | Official | 1,2,6,8/24 |
| VISA Hague JV Fleet Regatta | Norfolk Yacht and Country Club | In-League | 1 Division | | Official | 2/11 |