| Singles competition |
| 1. Ari Smolyar (MIDDMT) vs. Nicolas Chua (UCM) 2-6, 5-3, unfinished |
| 2. Noah Farrell (MIDDMT) def. Sven Kranz (UCM) 6-4, 6-3 |
| 3. Palmer Campbell (MIDDMT) vs. Deepak Sabada (UCM) 6-1, 5-7, unfinished |
| 4. Jackson Frons (MIDDMT) def. Peter Leung (UCM) 6-0, 6-4 |
| 5. William de Quant (MIDDMT) def. Luke Tsai (UCM) 6-2, 7-5 |
| 6. Kyle Schlanger (MIDDMT) vs. David Liu (UCM) 7-6 (7-1), 4-0, unfinished |
| Doubles competition |
| 1. Ankur Bhargava/Deepak Sabada (UCM) def. Palmer Campbell/Peter Heidrich (MIDDMT) 8-5 |
| 2. Noah Farrell/Ari Smolyar (MIDDMT) def. Max Hawkins/Luke Tsai (UCM) 9-7 |
| 3. William de Quant/Chris Frost (MIDDMT) def. Nicolas Chua/David Liu (UCM) 8-5 |
| Match Notes |
| Chicago (Ill.) 19-4; National ranking #8 |
| Middlebury 22-3; National ranking #3 |
| Order of finish: Doubles (1,3,2); Singles (,4,5,2) |
| Semifinals of the NCAA III Men's Tennis Championships |
| Middlebury advances to Wednesday's final against top-ranked CMS at 3:00 p.m. |
| T-3:14 A-100 |