NESSA Team Racing Results
| Date | School 1 | School 2 | Score 1 | Score 2 | Comments |
| 03/08/2009 | Brewster Academy | Cape Elizabeth HS | 2 | 0 | |
| 03/27/2009 | Prout School | Bishop Hendricken High School | 3 | 0 | |
| 03/28/2009 | East Greenwich High School | Westerly High School | 2 | 1 | |
| 03/28/2009 | Westerly High School | Bishop Hendricken High School | 3 | 0 | |
| 03/28/2009 | Tabor Academy | Marthas Vineyard RHS | 3 | 0 | |
| 03/28/2009 | Tabor Academy | East Greenwich High School | 3 | 0 | |
| 03/28/2009 | North Kingstown High School | Cheverus High School | 3 | 0 | |
| 03/28/2009 | Tabor Academy | North Kingstown High School | 2 | 1 | |
| 03/28/2009 | Tabor Academy | Cheverus High School | 3 | 0 | |
| 03/28/2009 | Marthas Vineyard RHS | East Greenwich High School | 2 | 1 | |
| 03/28/2009 | Marthas Vineyard RHS | North Kingstown High School | 2 | 1 | |
| 03/28/2009 | Cheverus High School | East Greenwich High School | 2 | 1 | |
| 03/28/2009 | Williams School | Greenwich Academy | 2 | 0 | |
| 03/28/2009 | Williams School | Greenwich High School | 2 | 0 | |
| 03/28/2009 | Williams School | Xavier High School | 2 | 1 | |
| 03/28/2009 | Manchester/Essex Regional High School | Boston College High School | 3 | 2 | |
| 03/28/2009 | Xavier High School | Greenwich Academy | 2 | 0 | |
| 03/28/2009 | Greenwich High School | Xavier High School | 2 | 1 | |
| 03/29/2009 | Hotchkiss School | Cape Elizabeth HS | 2 | 0 | |
| 03/31/2009 | Sharon High School | Bishop Stang High School | 3 | 2 | |
| 03/31/2009 | Harwich High School | Chatham High School | 3 | 0 | |
| 03/31/2009 | Prout School | St. Mary's Academy - Bay View | 2 | 0 | |
| 03/31/2009 | Prout School | Mount Saint Charles Academy | 2 | 0 | |
| 04/01/2009 | Brewster Academy | Manchester/Essex Regional High School | 3 | 2 | |
| 04/01/2009 | Boston College High School | Hingham High School | 3 | 2 | |
| 04/01/2009 | Portsmouth Abbey School | Moses Brown School | 3 | 2 | |
| 04/01/2009 | Duxbury High School | St John's Prep | 4 | 0 | |
| 04/01/2009 | Nauset Regional High School | Falmouth High School | 3 | 0 | |
| 04/01/2009 | North Kingstown High School | St. Mary's Academy - Bay View | 5 | 0 | |
| 04/01/2009 | Fairfield Prep | Staples High School | 2 | 0 | |
| 04/01/2009 | Greens Farms Academy | Greenwich Academy | 2 | 0 | |
| 04/01/2009 | Darien High School | Greenwich High School | 2 | 0 | |
| 04/02/2009 | Marthas Vineyard RHS | Harwich High School | 3 | 0 | |
| 04/02/2009 | Marthas Vineyard RHS | Barnstable HS | 3 | 0 | |
| 04/02/2009 | Xavier High School | Fairfield Prep | 3 | 1 | |
| 04/02/2009 | Nauset Regional High School | Chatham High School | 3 | 0 | |
| 04/02/2009 | Barrington High School | Portsmouth High School (RI) | 4 | 1 | |
| 04/04/2009 | Duxbury High School | Portsmouth Abbey School | 3 | 2 | |
| 04/04/2009 | East Lyme High School | Daniel Hand HS | 3 | 0 | |
| 04/04/2009 | Xavier High School | East Lyme High School | 3 | 1 | |
| 04/04/2009 | Xavier High School | Daniel Hand HS | 3 | 0 | |
| 04/04/2009 | Manchester/Essex Regional High School | Marblehead High School | 3 | 2 | |
| 04/04/2009 | Manchester/Essex Regional High School | George Stevens Academy | 3 | 0 | |
| 04/04/2009 | Tabor Academy | Bishop Stang High School | 4 | 1 | |
| 04/04/2009 | George Stevens Academy | Marblehead High School | 3 | 2 | |
| 04/04/2009 | Boston College High School | Cape Cod Academy | 2 | 0 | |
| 04/05/2009 | Greenwich High School | Fairfield Prep | 2 | 1 | |
| 04/05/2009 | Brunswick School | Greens Farms Academy | 3 | 0 | |
| 04/05/2009 | Fairfield Prep | Brunswick School | 3 | 0 | |
| 04/05/2009 | Darien High School | Greens Farms Academy | 3 | 0 | |
| 04/05/2009 | Fairfield Prep | Greens Farms Academy | 2 | 1 | |
| 04/05/2009 | Darien High School | Brunswick School | 2 | 0 | |
| 04/05/2009 | Greenwich High School | Greens Farms Academy | 2 | 1 | |
| 04/05/2009 | Darien High School | Fairfield Prep | 2 | 0 | |
| 04/05/2009 | Greenwich High School | Brunswick School | 2 | 0 | |
| 04/05/2009 | Darien High School | Greenwich High School | 2 | 0 | |
| 04/05/2009 | Manchester/Essex Regional High School | George Stevens Academy | 3 | 0 | This is a different meet on a different day |
| 04/05/2009 | Boston College High School | Cheverus High School | 3 | 0 | |
| 04/05/2009 | Hingham High School | Portland HS | 2 | 1 | |
| 04/05/2009 | Hingham High School | Cape Elizabeth HS | 2 | 0 | |
| 04/05/2009 | Nantucket High School | Marthas Vineyard RHS | 3 | 0 | |
| 04/05/2009 | Darien High School | Hotchkiss School | 2 | 1 | |
| 04/05/2009 | Hotchkiss School | Greenwich High School | 2 | 0 | |
| 04/05/2009 | Hotchkiss School | Brunswick School | 2 | 0 | |
| 04/05/2009 | Hotchkiss School | Greens Farms Academy | 2 | 0 | |
| 04/05/2009 | Hotchkiss School | Fairfield Prep | 2 | 0 | |
| 04/05/2009 | Brewster Academy | Marblehead High School | 3 | 0 | |
| 04/05/2009 | Brewster Academy | George Stevens Academy | 3 | 0 | |
| 04/05/2009 | Brewster Academy | Manchester/Essex Regional High School | 2 | 1 | |
| 04/07/2009 | Nauset Regional High School | Sandwich High School | 3 | 0 | |
| 04/07/2009 | St John's Prep | Belmont Hill School | 3 | 2 | |
| 04/07/2009 | Moses Brown School | Sharon High School | 5 | 0 | |
| 04/07/2009 | East Greenwich High School | Portsmouth High School (RI) | 3 | 0 | |
| 04/08/2009 | St George's School | Tabor Academy | 3 | 2 | |
| 04/08/2009 | Portsmouth Abbey School | Milton Academy | 4 | 1 | |
| 04/08/2009 | Boston College High School | St John's Prep | 3 | 1 | |
| 04/08/2009 | Duxbury High School | Manchester/Essex Regional High School | 3 | 0 | |
| 04/08/2009 | Barnstable HS | Cape Cod Academy | 3 | 0 | |
| 04/08/2009 | Williams School | Daniel Hand HS | 2 | 1 | |
| 04/08/2009 | Xavier High School | Williams School | 3 | 1 | |
| 04/08/2009 | Staples High School | Greenwich Academy | 2 | 0 | |
| 04/08/2009 | Greens Farms Academy | Greenwich High School | 2 | 0 | |
| 04/08/2009 | Greenwich High School | Greenwich Academy | 3 | 0 | |
| 04/08/2009 | Greens Farms Academy | Staples High School | 2 | 0 | |
| 04/08/2009 | Greens Farms Academy | Greenwich Academy | 2 | 0 | second meet on the same day |
| 04/08/2009 | Staples High School | Greenwich High School | 2 | 1 | |
| 04/09/2009 | Cape Cod Academy | Falmouth High School | 3 | 0 | |
| 04/09/2009 | Dennis-Yarmouth HS | Bourne High School | 5 | 0 | |
| 04/09/2009 | Providence Country Day School | Barrington High School | 4 | 1 | |
| 04/09/2009 | Hingham High School | St John's Prep | 3 | 2 | |
| 04/09/2009 | East Greenwich High School | East Lyme High School | 4 | 0 | |
| 04/09/2009 | Westerly High School | Prout School | 2 | 1 | |
| 04/09/2009 | Barnstable HS | Chatham High School | 3 | 0 | |
| 04/09/2009 | Bishop Stang High School | Dartmouth High School | 3 | 2 | |
| 04/09/2009 | Wellesley High School | Boston Latin School | 2 | 3 | |
| 04/09/2009 | Daniel Hand HS | Sound School | 2 | 1 | |
| 04/10/2009 | Bourne High School | Chatham High School | 3 | 2 | |
| 04/11/2009 | Portsmouth Abbey School | North Kingstown High School | 3 | 0 | |
| 04/11/2009 | Moses Brown School | Hotchkiss School | 3 | 2 | |
| 04/11/2009 | St George's School | Falmouth High School | 3 | 0 | |
| 04/11/2009 | Tabor Academy | Barnstable HS | 5 | 0 | |
| 04/11/2009 | Tabor Academy | Dartmouth High School | 3 | 1 | |
| 04/11/2009 | Cheverus High School | Brewster Academy | 3 | 0 | |
| 04/11/2009 | Portland HS | Cape Elizabeth HS | 3 | 0 | |
| 04/13/2009 | Dennis-Yarmouth HS | Falmouth High School | 3 | 0 | |
| 04/13/2009 | Nantucket High School | Nauset Regional High School | 3 | 2 | |
| 04/13/2009 | Lincoln Sudbury Regional High School | Wellesley High School | 3 | 2 | |
| 04/13/2009 | Bishop Hendricken High School | Rocky Hill School | 4 | 1 | |
| 04/14/2009 | Barnstable HS | Dennis-Yarmouth HS | 3 | 0 | |
| 04/14/2009 | Lincoln Sudbury Regional High School | Dover Sherborn RHS | 5 | 0 | |
| 04/14/2009 | Nauset Regional High School | Sandwich High School | 3 | 0 | |
| 04/14/2009 | St John's Prep | Brookline High | 4 | 1 | |
| 04/14/2009 | Duxbury High School | Bishop Stang High School | 4 | 0 | |
| 04/14/2009 | East Greenwich High School | Dartmouth High School | 3 | 2 | |
| 04/14/2009 | Marthas Vineyard RHS | Bourne High School | 3 | 1 | |
| 04/14/2009 | Sharon High School | Hingham High School | 3 | 2 | |
| 04/14/2009 | Harwich High School | Chatham High School | 3 | 1 | |
| 04/15/2009 | Darien High School | Greenwich Academy | 2 | 0 | |
| 04/15/2009 | Greens Farms Academy | Brunswick School | 2 | 1 | |
| 04/15/2009 | Brunswick School | Greenwich Academy | 3 | 0 | |
| 04/15/2009 | Darien High School | Greens Farms Academy | 2 | 0 | |
| 04/15/2009 | Greens Farms Academy | Greenwich Academy | 2 | 0 | |
| 04/15/2009 | Darien High School | Brunswick School | 2 | 0 | |
| 04/15/2009 | Winchester High School | Boston Latin School | 3 | 2 | |
| 04/15/2009 | Boston College High School | Tabor Academy | 3 | 2 | |
| 04/15/2009 | Tabor Academy | Portsmouth Abbey School | 4 | 1 | |
| 04/15/2009 | Hingham High School | Belmont Hill School | 3 | 1 | |
| 04/15/2009 | East Greenwich High School | Providence Country Day School | 2 | 1 | |
| 04/15/2009 | East Greenwich High School | Bishop Hendricken High School | 2 | 0 | |
| 04/15/2009 | Providence Country Day School | Bishop Hendricken High School | 2 | 0 | |
| 04/15/2009 | Bishop Hendricken High School | Rocky Hill School | 2 | 1 | |
| 04/15/2009 | Providence Country Day School | Rocky Hill School | 2 | 0 | |
| 04/15/2009 | Rocky Hill School | East Greenwich High School | 2 | 0 | |
| 04/15/2009 | St John's Prep | BB&N - Buckingham Browne and Nichols | 4 | 0 | |
| 04/15/2009 | Lincoln Sudbury Regional High School | Notre Dame Academy | 4 | 1 | |
| 04/15/2009 | Sharon High School | North Kingstown High School | 3 | 2 | |
| 04/15/2009 | Dennis-Yarmouth HS | Chatham High School | 3 | 0 | |
| 04/15/2009 | Duxbury High School | Cape Cod Academy | 4 | 1 | |
| 04/15/2009 | Wellesley High School | Dover Sherborn RHS | 4 | 0 | |
| 04/16/2009 | St George's School | Boston College High School | 3 | 0 | |
| 04/16/2009 | Sharon High School | Manchester/Essex Regional High School | 3 | 2 | |
| 04/16/2009 | North Kingstown High School | East Lyme High School | 3 | 1 | |
| 04/16/2009 | Sandwich High School | Dennis-Yarmouth HS | 3 | 2 | |
| 04/16/2009 | Bourne High School | Harwich High School | 3 | 2 | |
| 04/16/2009 | Nantucket High School | Bourne High School | 4 | 1 | |
| 04/16/2009 | Dartmouth High School | Nauset Regional High School | 4 | 1 | |
| 04/17/2009 | Portsmouth Abbey School | Cape Cod Academy | 4 | 1 | |
| 04/17/2009 | Sandwich High School | Harwich High School | 3 | 1 | |
| 04/17/2009 | Duxbury High School | BB&N - Buckingham Browne and Nichols | 2 | 0 | |
| 04/17/2009 | St George's School | East Greenwich High School | 3 | 0 | |
| 04/18/2009 | Duxbury High School | Milton Academy | 3 | 0 | |
| 04/18/2009 | Duxbury High School | Tabor Academy | 3 | 2 | |
| 04/18/2009 | Milton Academy | Manchester/Essex Regional High School | 1 | 0 | Forfeit by MERSH |
| 04/18/2009 | Hotchkiss School | Darien High School | 2 | 0 | |
| 04/18/2009 | Portsmouth Abbey School | Darien High School | 2 | 1 | |
| 04/18/2009 | Hotchkiss School | Portsmouth Abbey School | 2 | 0 | |
| 04/18/2009 | Sharon High School | St John's Prep | 4 | 1 | |
| 04/18/2009 | Greenwich High School | East Lyme High School | 3 | 0 | |
| 04/18/2009 | Williams School | Moses Brown School | 2 | 1 | |
| 04/18/2009 | Moses Brown School | East Lyme High School | 2 | 0 | |
| 04/18/2009 | Williams School | Greenwich High School | 2 | 0 | |
| 04/18/2009 | Moses Brown School | Greenwich High School | 2 | 0 | |
| 04/18/2009 | Williams School | East Lyme High School | 2 | 0 | |
| 04/18/2009 | Tabor Academy | Milton Academy | 3 | 2 | |
| 04/18/2009 | Duxbury High School | Manchester/Essex Regional High School | 5 | 0 | |
| 04/18/2009 | Tabor Academy | Greenwich Academy | 3 | 0 | |
| 04/19/2009 | Milton Academy | Greenwich High School | 2 | 0 | |
| 04/20/2009 | Tabor Academy | Manchester/Essex Regional High School | 3 | 0 | |
| 04/20/2009 | Moses Brown School | Providence Country Day School | 3 | 0 | |
| 04/20/2009 | Westerly High School | St. Mary's Academy - Bay View | 3 | 2 | |
| 04/21/2009 | Portsmouth Abbey School | East Greenwich High School | 4 | 0 | |
| 04/21/2009 | Moses Brown School | St. Mary's Academy - Bay View | 3 | 0 | |
| 04/22/2009 | Tabor Academy | Moses Brown School | 4 | 1 | |
| 04/22/2009 | Darien High School | Brunswick School | 2 | 0 | |
| 04/22/2009 | Duxbury High School | Dartmouth High School | 5 | 0 | |
| 04/22/2009 | Westerly High School | Rogers High School | 3 | 2 | |
| 04/22/2009 | Barnstable HS | Boston College High School | 3 | 1 | |
| 04/22/2009 | Milton Academy | Boston College High School | 2 | 1 | |
| 04/22/2009 | Milton Academy | Barnstable HS | 2 | 0 | |
| 04/22/2009 | Staples High School | Fairfield Prep | 2 | 0 | |
| 04/22/2009 | St George's School | Portsmouth Abbey School | 5 | 0 | |
| 04/22/2009 | Greens Farms Academy | Greenwich Academy | 2 | 0 | |
| 04/22/2009 | North Kingstown High School | East Greenwich High School | 4 | 1 | |
| 04/22/2009 | Williams School | Bishop Hendricken High School | 4 | 1 | |
| 04/23/2009 | Prout School | Barrington High School | 3 | 0 | |
| 04/23/2009 | North Kingstown High School | Moses Brown School | 3 | 2 | |
| 04/23/2009 | St George's School | Rogers High School | 2 | 0 | |
| 04/24/2009 | Boston College High School | Sharon High School | 3 | 2 | |
| 04/24/2009 | Portsmouth Abbey School | Bishop Hendricken High School | 5 | 0 | |
| 04/24/2009 | North Kingstown High School | Providence Country Day School | 4 | 1 | |
| 04/27/2009 | Moses Brown School | East Greenwich High School | 3 | 0 | |
| 04/27/2009 | Xavier High School | Fairfield Prep | 2 | 1 | |
| 04/27/2009 | Manchester/Essex Regional High School | Brookline High | 2 | 1 | |
| 04/27/2009 | Rogers High School | Prout School | 3 | 2 | |
| 04/27/2009 | Marthas Vineyard RHS | Dennis-Yarmouth HS | 5 | 0 | |
| 04/27/2009 | Falmouth High School | Sandwich High School | 3 | 2 | |
| 04/27/2009 | St George's School | North Kingstown High School | 4 | 1 | |
| 04/27/2009 | Dartmouth High School | Barnstable HS | 3 | 0 | |
| 04/28/2009 | Dover Sherborn RHS | Notre Dame Academy | 3 | 2 | |
| 04/28/2009 | Sharon High School | Brookline High | 4 | 0 | |
| 04/28/2009 | Nauset Regional High School | Chatham High School | 3 | 1 | |
| 04/28/2009 | Notre Dame Academy | St. Sebastian's Country Day School | 1 | 0 | Forfeited by St Sebs |
| 04/28/2009 | Providence Country Day School | Prout School | 3 | 0 | |
| 04/28/2009 | North Kingstown High School | Westerly High School | 5 | 0 | |
| 04/28/2009 | Williams School | East Lyme High School | 5 | 0 | |
| 04/28/2009 | Xavier High School | Sound School | 2 | 1 | |
| 04/29/2009 | Rogers High School | Rocky Hill School | 3 | 2 | |
| 04/29/2009 | St. Mary's Academy - Bay View | Portsmouth High School (RI) | 2 | 0 | |
| 04/29/2009 | Bishop Hendricken High School | Portsmouth High School (RI) | 2 | 1 | |
| 04/29/2009 | St. Mary's Academy - Bay View | Bishop Hendricken High School | 2 | 0 | |
| 04/29/2009 | East Greenwich High School | Bishop Stang High School | 3 | 2 | |
| 04/29/2009 | Xavier High School | Sound School | 3 | 0 | |
| 04/29/2009 | Darien High School | Staples High School | 2 | 1 | |
| 04/29/2009 | Darien High School | Brunswick School | 2 | 0 | |
| 04/29/2009 | Duxbury High School | Hingham High School | 3 | 0 | |
| 04/29/2009 | St George's School | Tabor Academy | 5 | 0 | |
| 04/29/2009 | Hingham High School | Barnstable HS | 2 | 1 | |
| 04/29/2009 | Portsmouth Abbey School | Providence Country Day School | 3 | 2 | |
| 04/29/2009 | Brewster Academy | Portland HS | 2 | 0 | |
| 04/29/2009 | Brewster Academy | Cheverus High School | 2 | 1 | |
| 04/29/2009 | Brewster Academy | Cape Elizabeth HS | 2 | 0 | |
| 04/29/2009 | St John's Prep | Manchester/Essex Regional High School | 4 | 1 | |
| 04/29/2009 | East Greenwich High School | Bishop Stang High School | 3 | 2 | |
| 04/29/2009 | Sharon High School | BB&N - Buckingham Browne and Nichols | 4 | 0 | |
| 04/29/2009 | Belmont Hill School | Portsmouth Abbey School | 3 | 2 | |
| 04/29/2009 | Greenwich High School | Greens Farms Academy | 2 | 0 | |
| 04/29/2009 | Staples High School | Brunswick School | 2 | 0 | |
| 04/29/2009 | Darien High School | Greenwich Academy | 2 | 0 | |
| 04/29/2009 | Staples High School | Greenwich Academy | 2 | 0 | |
| 04/29/2009 | Duxbury High School | Barnstable HS | 3 | 0 | |
| 04/29/2009 | Moses Brown School | Dartmouth High School | 3 | 2 | |
| 04/29/2009 | Marthas Vineyard RHS | Chatham High School | 3 | 0 | |
| 04/30/2009 | Marthas Vineyard RHS | Dartmouth High School | 3 | 2 | |
| 04/30/2009 | St. Mary's Academy - Bay View | Barrington High School | 3 | 2 | |
| 04/30/2009 | Brunswick School | Greenwich Academy | 3 | 2 | |
| 04/30/2009 | Duxbury High School | Boston College High School | 4 | 0 | |
| 04/30/2009 | Williams School | Branford High School | 4 | 0 | |
| 04/30/2009 | Dennis-Yarmouth HS | Bourne High School | 3 | 0 | |
| 04/30/2009 | Sandwich High School | Chatham High School | 3 | 0 | |
| 04/30/2009 | Sharon High School | East Greenwich High School | 3 | 2 | |
| 04/30/2009 | Hingham High School | Manchester/Essex Regional High School | 3 | 0 | |
| 04/30/2009 | Moses Brown School | Bishop Stang High School | 3 | 1 | |
| 04/30/2009 | Barnstable HS | Bishop Stang High School | 5 | 0 | |
| 04/30/2009 | Darien High School | Fairfield Prep | 2 | 1 | |
| 04/30/2009 | Darien High School | Fairfield Prep | 2 | 0 | make-up regatta |
| 04/30/2009 | Winchester High School | Dover Sherborn RHS | 5 | 0 | |
| 04/30/2009 | Winchester High School | Wellesley High School | 3 | 2 | |
| 05/01/2009 | Tabor Academy | Cape Cod Academy | 5 | 0 | |
| 05/01/2009 | Tabor Academy | St John's Prep | 5 | 0 | |
| 05/01/2009 | Providence Country Day School | East Greenwich High School | 3 | 0 | |
| 05/01/2009 | Providence Country Day School | Barrington High School | 3 | 0 | |
| 05/01/2009 | East Greenwich High School | Barrington High School | 3 | 0 | |
| 05/01/2009 | Boston College High School | Bishop Stang High School | 1 | 0 | Forfeited by Bishop Stang |
| 05/01/2009 | Portsmouth Abbey School | Dartmouth High School | 4 | 0 | |
| 05/01/2009 | Hingham High School | Brookline High | 3 | 0 | |
| 05/02/2009 | Belmont Hill School | Manchester/Essex Regional High School | 3 | 2 | |
| 05/02/2009 | Hotchkiss School | Barnstable HS | 3 | 0 | |
| 05/02/2009 | Hotchkiss School | Cheverus High School | 3 | 0 | |
| 05/02/2009 | Hotchkiss School | Fairfield Prep | 1 | 0 | Forfeit due to SATs |
| 05/02/2009 | Barnstable HS | Cheverus High School | 3 | 2 | |
| 05/02/2009 | Barnstable HS | Fairfield Prep | 1 | 0 | forfeited due to SATs |
| 05/02/2009 | Cheverus High School | Fairfield Prep | 1 | 0 | forfeit due to SATs |
| 05/02/2009 | Dartmouth High School | East Lyme High School | 2 | 1 | |
| 05/02/2009 | St George's School | Williams School | 3 | 0 | |
| 05/02/2009 | Williams School | Dartmouth High School | 2 | 0 | |
| 05/02/2009 | St George's School | East Lyme High School | 2 | 0 | |
| 05/02/2009 | St George's School | Dartmouth High School | 2 | 0 | |
| 05/02/2009 | Tabor Academy | Nantucket High School | 5 | 0 | |
| 05/02/2009 | Tabor Academy | Falmouth High School | 4 | 1 | |
| 05/02/2009 | Milton Academy | Moses Brown School | 3 | 0 | |
| 05/02/2009 | Nauset Regional High School | Cape Cod Academy | 3 | 2 | |
| 05/02/2009 | St George's School | Bishop Stang High School | 3 | 1 | |
| 05/02/2009 | Cape Cod Academy | Marthas Vineyard RHS | 3 | 2 | |
| 05/02/2009 | Marthas Vineyard RHS | Nauset Regional High School | 2 | 0 | Meet shorten due by agreement/Transport issues |
| 05/03/2009 | Barnstable HS | Bourne High School | 3 | 0 | |
| 05/03/2009 | Nantucket High School | Bourne High School | 3 | 1 | |
| 05/03/2009 | Barnstable HS | Nantucket High School | 3 | 1 | |
| 05/03/2009 | Barnstable HS | Nantucket High School | 2 | 1 | different meet/ same day |
| 05/03/2009 | Boston College High School | Xavier High School | 2 | 1 | |
| 05/03/2009 | Hotchkiss School | Cheverus High School | 2 | 0 | |
| 05/04/2009 | Dennis-Yarmouth HS | Sandwich High School | 3 | 0 | |
| 05/04/2009 | Nauset Regional High School | Bourne High School | 3 | 0 | |
| 05/04/2009 | Falmouth High School | Chatham High School | 4 | 0 | |
| 05/04/2009 | Sharon High School | Wellesley High School | 3 | 1 | |
| 05/04/2009 | Moses Brown School | Providence Country Day School | 3 | 0 | |
| 05/04/2009 | Rogers High School | Rocky Hill School | 3 | 0 | |
| 05/05/2009 | Westerly High School | Prout School | 2 | 1 | |
| 05/05/2009 | Nauset Regional High School | Dennis-Yarmouth HS | 3 | 1 | |
| 05/06/2009 | Falmouth High School | Harwich High School | 2 | 1 | |
| 05/06/2009 | Sharon High School | Winchester High School | 3 | 1 | |
| 05/06/2009 | Nauset Regional High School | Harwich High School | 3 | 0 | |
| 05/06/2009 | Nauset Regional High School | Falmouth High School | 2 | 0 | |
| 05/06/2009 | Sound School | Salisbury School | 2 | 1 | |
| 05/06/2009 | Bishop Stang High School | Portsmouth Abbey School | 3 | 2 | |
| 05/06/2009 | Rogers High School | Portsmouth High School (RI) | 3 | 0 | |
| 05/07/2009 | Winchester High School | Notre Dame Academy | 5 | 0 | |
| 05/07/2009 | Barnstable HS | Nauset Regional High School | 3 | 1 | |
| 05/07/2009 | Dennis-Yarmouth HS | Marthas Vineyard RHS | 1 | 0 | Forfeit by MV |
| 05/07/2009 | Wellesley High School | Dover Sherborn RHS | 3 | 0 | |
| 05/08/2009 | Falmouth High School | Barnstable HS | 3 | 0 | |
| 05/08/2009 | Providence Country Day School | Bishop Hendricken High School | 3 | 0 | |
| 05/11/2009 | Lincoln Sudbury Regional High School | BB&N - Buckingham Browne and Nichols | 3 | 0 | |
| 05/11/2009 | Barnstable HS | Dennis-Yarmouth HS | 3 | 0 | |
| 05/11/2009 | Sharon High School | Sandwich High School | 4 | 0 | |
| 05/11/2009 | Bourne High School | Chatham High School | 3 | 0 | |
| 05/12/2009 | Rogers High School | Barrington High School | 3 | 0 | |
| 05/12/2009 | Dennis-Yarmouth HS | Chatham High School | 3 | 0 | |
| 05/12/2009 | Wellesley High School | Notre Dame Academy | 3 | 2 | |
| 05/12/2009 | Barnstable HS | Sandwich High School | 3 | 0 | |
| 05/12/2009 | Sharon High School | Lincoln Sudbury Regional High School | 3 | 2 | |
| 05/13/2009 | Fairfield Prep | Greenwich High School | 2 | 1 | |
| 05/13/2009 | Bishop Stang High School | Bourne High School | 3 | 0 | |
| 05/13/2009 | Dartmouth High School | Bourne High School | 3 | 0 | |
| 05/13/2009 | Barnstable HS | Nauset Regional High School | 3 | 2 | |
| 05/13/2009 | Belmont Hill School | St John's Prep | 3 | 2 | |
| 05/13/2009 | Daniel Hand HS | Branford High School | 2 | 1 | |
| 05/13/2009 | Rogers High School | Moses Brown School | 3 | 2 | |
| 05/14/2009 | Nantucket High School | Dennis-Yarmouth HS | 3 | 0 | |
| 05/15/2009 | Nantucket High School | Falmouth High School | 2 | 0 | |
| 05/15/2009 | Providence Country Day School | Bishop Stang High School | 4 | 1 | |
| 05/15/2009 | Harwich High School | Bourne High School | 3 | 0 | |
| 05/18/2009 | Bishop Stang High School | Dennis-Yarmouth HS | 3 | 2 | |
| 05/18/2009 | Sandwich High School | Chatham High School | 3 | 0 | |
| 05/19/2009 | Nauset Regional High School | Dennis-Yarmouth HS | 3 | 2 | |
| 05/19/2009 | Marthas Vineyard RHS | Nantucket High School | 4 | 1 | |
| 05/19/2009 | Sandwich High School | Falmouth High School | 3 | 2 | |
| 05/20/2009 | Falmouth High School | Chatham High School | 3 | 2 | |
| 05/20/2009 | Nantucket High School | Bourne High School | 3 | 0 | |
| 05/20/2009 | Barnstable HS | Harwich High School | 3 | 1 | |
| 05/20/2009 | Sandwich High School | Barnstable HS | 3 | 0 | |
| 05/20/2009 | Nauset Regional High School | Bishop Stang High School | 3 | 2 | |
| 05/21/2009 | Nantucket High School | Chatham High School | 3 | 0 | |
| 05/21/2009 | Dennis-Yarmouth HS | Harwich High School | 3 | 1 | |
| 05/22/2009 | Sandwich High School | Bourne High School | 3 | 1 | |
| 05/26/2009 | Dennis-Yarmouth HS | Falmouth High School | 3 | 0 | |
| 05/26/2009 | Nauset Regional High School | Harwich High School | 3 | 0 | |
| 05/26/2009 | Bishop Stang High School | Prout School | 4 | 1 | |
| 05/27/2009 | Falmouth High School | Bourne High School | 1 | 0 | forfeited by BHS b/c of too few sailors. |
| 05/27/2009 | Nantucket High School | Harwich High School | 3 | 0 |