| 1999 Schedule | |||
| September | |||
| 14 | St. Joseph's | W 3-0 | |
| 17-18 | @ Bates Round Robin | W 1, L 2 | |
| Bates 0-3; Gordon 2-3; St. Michael's 3-0 | |||
| 22 | Bowdoin | W 3-2 | |
| 24-25 | @ MIT Invitational | W 0, L 4 | |
| MIT 0-3; Wheaton 1-3; Skidmore 1-3; | |||
| Smith 0-3 | |||
| 29 | UMaine-Farmington | W 3-0 | |
| October | |||
| 1-2 | @ Bates Invitational | W 1, L 3 | |
| Springfield 0-3, W. Conn.S.U. 3-1 | |||
| Brandeis 0-3, Wheaton 1-3 | |||
| 6 | @ Bates | L 3-1 | |
| 9 | @ Bowdoin Round Robin | 10am | |
| 13 | @ U New England | W 3-0 | |
| 16 | @ NESCAC Quad. Trinity | W 3, L 0 | |
| Hamilton 0-3, Trinity College 2-3, Conn. 0-3 | |||
| 23-24 | Colby Invitational | W 1 , L 0 | |
| 27 | @ USM | W 3-0 | |
| 29-30 | @ Maine State Champs. UMaine-Machias | W 2, L 1 U Maine-Presque Isle 3-0 Bowdoin 3-2 Bates 0-3 | |
| November | |||
| 5-6 | @ NESCAC Champs. Trinity | W 1, L 2 Conn W 3-0 Middlebury L 3-0 Trinity L 3-1 | |