| Round of 128 | L Jeff HudsonSt. Olaf def. Mike AroSt. Scholastica | 6-2, 6-1 |
| Round of 128 | L Brandon StensethUW-La Crosse def. Cullen CombsSt. Scholastica | 6-3, 6-1 |
| Round of 128 | L Andrew CarlosUW-Eau Claire def. Erik ConleySt. Scholastica | 6-2, 4-6, 1-0 (10-5) |
| Round of 128 | L Juan MontenegroMSOE def. Nick LindSt. Scholastica | 6-1, 6-4 |
| Round of 64 | W Alex NagleSt. Scholastica def. Michael BradenConcordia University (Wis.) | 6-1, 6-2 |
| Round of 64 | W Tom SchneuerSt. Scholastica def. Taylor ShafferConcordia University (Wis.) | 7-5, 6-3 |
| Round of 64 | L David BloomquistConcordia-Moorhead def. Brian LindbergSt. Scholastica | 6-3, 3-6, 1-0 (10-6) |
| Round of 64 | L Anthony BarthouseMSOE def. Kolin DeanSt. Scholastica | 7-6 (7-4), 4-6, 1-0 (12-10) |
| Round of 32 | L Mark SchadlerMSOE def. Alex NagleSt. Scholastica | 6-0, 6-1 |
| Round of 32 | L Charlie ReinertsenSt. Olaf def. Tom SchneuerSt. Scholastica | 6-1, 6-1 |
