| Natan Spear (NW) def. Zachary Schwartz (WIS) 6-1, 6-2 |
| Graydon Lair (MSU) def. Robin Parts (WIS) 6-4, 1-6, 6-7 (4-0) |
| Jared Pratt (WIS) def. Felix Nordby (NW) 3-6, 6-3, 6-4 |
| Sebastian Vile (WIS) def. William Gleason (NEB) 6-3, 6-1 |
| Max Bengtsson (NW) def. Mihailo Popovic (WIS) 6-7 (4-0), 3-6 |
| Patrick Fletchall (IU) def. Robin Parts (WIS) 6-1, 6-7 (6-0), 6-4 |
| Sebastian Vile (WIS) def. Gleb Blehker (NW) 6-4, 6-4 |
| Jared Pratt (WIS) def. Roni Hietaranta (NEB) 6-7 (4-0), 6-3, 5-7 |
| Patorn Hanchaikul (MICH) def. Mihailo Popovic (WIS) 6-4, 6-4 |
| Mujtaba Ali-Khan (PUR) def. Zachary Schwartz (WIS) 7-6 (0-5), 6-3 |
| Tomasz Dudek (PUR) def. Robin Parts (WIS) 6-3, 6-7 (4-0), 10-12 |
| Ekansh Kumar (IU) def. Robin Parts (WIS) 6-4, 2-6, 10-3 |
| Sebastian Vile (WIS) def. Ilya Tiraspolsky (IU) 4-6, 6-0, 6-4 |
| Sebastian Vile (WIS) def. Roni Hietaranta (NEB) 6-4, 6-1 |
| Mihailo Popovic (WIS) def. Shunya Maruyama (NEB) 6-4, 6-1 |
| Zachary Schwartz (WIS) def. Luc Boulier (IU) 6-4, 6-4 |
| Ivan Yatsuk (NW) def. Sebastian Vile (WIS) 6-2, 4-6, 6-2 |
