| 64 | JT Bilski (WESLEYAN) def. Caymus Choi (BOWDOIN) 6-3, 6-1 |
| 64 | Brett Keeling (WESLEYAN) def. Pete Sevikul (EMERSON) 6-0, 6-2 |
| 64 | Ben Mitchell (WESLEYAN) def. Logan Back (BABSON) 6-2, 6-1 |
| 32 | JT Bilski (WESLEYAN) def. Nathan Jackson (MIDD) 6-3, 7-5 |
| 32 | Brett Keeling (WESLEYAN) def. Jake Cohen (COLBY) 6-4, 5-7, 6-2 |
| 32 | Julian Wu (MIDD) def. Ben Mitchell (WESLEYAN) 6-2, 6-3 |
| 16 | JT Bilski (WESLEYAN) def. Andreas Sillaste (AMHERST) 7-6 (7-5), 7-5 |
| 16 | Dylan Walters (BRANDEIS) def. Brett Keeling (WESLEYAN) 7-6 (7-5), 6-2 |
| QF | Matt Kandel (WILLIAMS) def. JT Bilski (WESLEYAN) 6-3, 3-6, 6-1 |
| B64 | Max Lustgarten (WESLEYAN) def. Ben Adey (BATES) 8-1 |
| B64 | Harry Portnoy (WESLEYAN) def. Davide Mirza (TUFTS) 8-3 |
| B64 | Takehiro Shuda (TUFTS) def. Chase Kasday (WESLEYAN) 8-6 |
| B64 | Max Litton (WESLEYAN) def. Martin Mejia (BABSON) 8-4 |
| B32 | Max Lustgarten (WESLEYAN) def. Aarush Ganji (TUFTS) by default |
| B32 | Harry Collomb (WESLEYAN) def. Eli Criss (BATES) 8-1 |
| B32 | Harry Portnoy (WESLEYAN) def. John Pope (TRINITY) 8-5 |
| B32 | Max Litton (WESLEYAN) def. Jack Ginter (TRINITY) retired |
| B16 | Brandon Felcher (TRINITY) def. Max Lustgarten (WESLEYAN) 7-6 (8-6), 6-3 |
| B16 | Harry Collomb (WESLEYAN) def. Peter Wang (AMHERST) 6-4, 6-2 |
| B16 | Harry Portnoy (WESLEYAN) def. Ethan Ohm (AMHERST) 6-2, 2-6, 10-8 |
| B16 | Rex Harrison (AMHERST) def. Max Litton (WESLEYAN) 5-7, 6-1, 10-0 |
| BQF | Harry Collomb (WESLEYAN) def. Brandon Felcher (TRINITY) 6-0, 6-0 |
| BQF | Andrew Watson (BABSON) def. Harry Portnoy (WESLEYAN) 6-4, 4-6, 10-8 |
| BSF | Harry Collomb (WESLEYAN) def. Andrew Watson (BABSON) 6-3, 6-4 |
| BF | Harry Collomb (WESLEYAN) def. Rex Harrison (AMHERST) 7-6 (7-5), 2-6, 11-9 |
