| Singles competition |
| R64 | Noah Farrell (Middlebury) def. Zain Ali (Tufts) 6-0, 6-0 |
| R32 | Noah Farrell (Middlebury) def. Blake Norton (Nichols) 6-0, 6-1 |
| R16 | Noah Farrell (Middlebury) def. Brian Grodecki (Williams) 6-4, 6-1 |
| QF | Noah Farrell (Middlebury) def. Jose Raventos (Williams) 6-2, 7-6 (7-5) |
| SF | Noah Farrell (Middlebury) def. Steven Chen (Wesleyan) 6-1, 6-3 |
| F | Noah Farrell (Middlebury) def. Luke Tercek (Bowdoin) 7-6 (7-4), 6-1 |
| R64 | Ari Smolyar (Middlebury) def. Issac Thylen (Babson) 6-3, 6-3 |
| R32 | Ari Smolyar (Middlebury) def. Zach Bessette (Amherst) 4-6, 6-3, 6-1 |
| R16 | Ari Smolyar (Middlebury) def. Ben Rosen (Bates) 6-4, 7-5 |
| QF | Luke Tercek (Bowdoin) def. Ari Smolyar (Middlebury) 6-1, 6-4 |
| R64 | Allen Jackson (Middlebury) def. Dhruv Yadav (Wesleyan) 6-4, 7-5 |
| R32 | Allen Jackson (Middlebury) def. Tyler Adams (Univ. of Southern Maine) 6-3, 6-2 |
| R16 | Steven Chen (Wesleyan) def. Allen Jackson (Middlebury) 3-6, 6-0, 6-2 |
| R64 | Palmer Campbell (Middlebury) def. Eric Pierce (Endicott) 6-1, 6-1 |
| R32 | Luke Tercek (Bowdoin) def. Palmer Campbell (Middlebury) 6-3, 6-1 |
| R64 | Timo van der Geest (Middlebury) def. Court Honda (Springfield) 6-4, 6-0 |
| R32 | Timo van der Geest (Middlebury) def. Joachim Samson (Wesleyan) retired |
| R16 | Rohan Gupte (Tufts) def. Timo van der Geest (Middlebury) 6-2, 4-6, 6-3 |
| R64 | William de Quant (Middlebury) def. Carl Reid (Colby) 2-6, 6-2, 6-2 |
| R32 | Alex Cauneac (M.I.T.) def. William de Quant (Middlebury) 6-0, 7-6 (7-4) |