| Date | Opponent | Score | Nation | Region | ||||
| Nov 21, 2008 | CORNELL | L | ||||||
| Nov 22, 2008 | at | George Washington | W | |||||
| Dec 3, 2008 | PRINCETON | L | ||||||
| Dec 5, 2008 | at | Vassar | W | |||||
| * | Dec 6, 2008 | vs | Stanford | W | ||||
| * | Dec 6, 2008 | vs | St. Lawrence | W | ||||
| # | Dec 7, 2008 | at | Hamilton | W | ||||
| Jan 16, 2009 | vs | #17 St. Lawrence | W | |||||
| Jan 18, 2009 | vs | #13 Bowdoin | W | |||||
| Jan 18, 2009 | vs | #22 Northeastern | W | |||||
| Jan 18, 2009 | vs | #11 Bates | W | |||||
| Jan 21, 2009 | #7 PENNSYLVANIA | L | ||||||
| Jan 23, 2009 | vs | #20 Tufts | W | |||||
| Jan 24, 2009 | vs | Colby | W | |||||
| Jan 24, 2009 | vs | Denison | W | |||||
| Jan 24, 2009 | at | #3 Yale | L | |||||
| Jan 30, 2009 | #6 ROCHESTER | L | ||||||
| Feb 7, 2009 | #37 HAVERFORD | W | ||||||
| Feb 11, 2009 | at | #13 Navy | W | |||||
| Feb 20, 2009 | vs | #13 Brown | W | |||||
| Feb 21, 2009 | vs | #10 Williams | L | |||||
| Feb 22, 2009 | vs | #11 Bates | L | |||||
| Feb 27-28, 2009 | College Squash Association Championships -- Williamstown, Mass. -- | |||||||
| Schedule legend |