| Singles competition |
| Draw 1 |
| 64 | Nick White (Brandeis University) vs. bye () -- no result |
| Fred Rosenshteyn (Brandeis University) def. David Farah (Middlebury College) 7-6 (0-4), 6-4 |
| Teddy Fitzgibbons (Middlebury College) def. Steven Milo (Brandeis University) 6-0, 6-0 |
| Rich Bonfiglio (Trinity College) def. Simon Miller (Brandeis University) 6-4, 6-3 |
| 32 | Tim Berg (Bates College) def. Nick White (Brandeis University) 6-0, 6-1 |
| Matt Bettles (Bates College) def. Fred Rosenshteyn (Brandeis University) 6-2, 6-2 |
| Round 2 Consolation |
| 32 | Casey Grindon (Bowdoin) def. Fred Rosenshteyn (Brandeis University) 6-4, 6-2 |
| Ezra Bernstein (Brandeis University) def. Alex Jacobs (Bowdoin) 3-6, 7-5, 18-16 |
| Chris Lord (Bowdoin) def. Simon Miller (Brandeis University) 6-2, 6-1 |
| Moritz Koenig (Amherst College) def. Dave Yovanoff (Brandeis University) 6-2, 6-2 |
| David Farah (Middlebury College) def. Steven Milo (Brandeis University) 7-6 (3-0), 6-3 |
| Alec Parower (Middlebury College) def. Nick White (Brandeis University) 6-1, 6-2 |
| 16 | Casey Grindon (Bowdoin) def. Ezra Bernstein (Brandeis University) 6-4, 6-3 |