| Date | Results | |
| May 26-28, 2016 | NCAA Division III Singles/Doubles Champs -- Kalamazoo, Mich. | |
| May 25, 2016 | Bowdoin 5, Middlebury 0 | |
| May 24, 2016 | Middlebury 5, University of Chicago 2 | |
| May 23, 2016 | Middlebury 5, Washington U. 1 | |
| May 15, 2016 | Middlebury 5, Skidmore College 0 | |
| May 14, 2016 | Middlebury 5, Wilkes University 0 | |
| May 08, 2016 | Middlebury 5, Bowdoin 1 | |
| May 07, 2016 | Middlebury 5, Wesleyan (Conn.) 2 | |
| May 01, 2016 | Middlebury 7, Skidmore College 2 | |
| Apr 30, 2016 | Middlebury 9, Trinity 0 | |
| Apr 24, 2016 | Middlebury 9, Connecticut College 0 | |
| Apr 23, 2016 | Middlebury 7, Amherst 2 | |
| Apr 17, 2016 | Middlebury 5, Bowdoin 4 | |
| Apr 10, 2016 | Middlebury 7, Tufts 2 | |
| Apr 09, 2016 | Middlebury 8, Williams 1 | |
| Apr 02, 2016 | ClaremontMuddScripps 6, Middlebury 3 | |
| Mar 31, 2016 | UC-Riverside 5, Middlebury 2 | |
| Mar 29, 2016 | Middlebury 6, Pomona-Pitzer 3 | |
| Mar 28, 2016 | Middlebury 9, Biola University 0 | |
| Mar 27, 2016 | Middlebury 9, Lewis and Clark 0 | |
| Mar 26, 2016 | Middlebury 8, Concordia (Calif.) 1 | |
| Mar 19, 2016 | Middlebury 5, Wesleyan 4 | |
| Mar 12, 2016 | Middlebury 9, Hamilton 0 | |
| Mar 12, 2016 | Middlebury 9, Bates Men 0 | |
| Oct 24-25, 2015 | Boston Invitational -- Boston, Mass. | |
| Oct 15-18, 2015 | USTA/ITA Small College Championships -- Sumter, South Carolina | |
| Oct 10-11, 2015 | Dartmouth Invitational -- Dartmouth College | |
| Oct 10-11, 2015 | Wallach Invitational -- Lewiston, Maine | |
| Sep 25-27, 2015 | USTA/ITA New England Regional -- Williamstown, Mass. | |
| Sep 19-20, 2015 | 2015 Middlebury Invitational -- Middlebury, Vt. | |