| Round of 128 | L Brady PorterUW-Whitewater def. Brian LindbergSt. Scholastica | 6-1, 6-2 |
| Round of 128 | Knute GundersenSt. Olaf College def. Brian TresedderConcordia University | 6-0, 6-0 |
| Round of 128 | Connor CunninghamGrinnell College def. Chris FowlerMacalester | 7-6 (7-3), 6-4 |
| Round of 128 | Jon ArandaCarleton College def. Coy WiegmannWartburg College | 6-0, 6-0 |
| Round of 128 | Ethan NiquetUW-Whitewater def. Quinn FoleyLuther College | 6-4, 6-1 |
| Round of 128 | Nic SchultzCarroll College def. Steven SkanseUniversity of St. Thomas | 4-6, 6-2, 10-6 |
| Round of 128 | Dan VollmmanCarleton College def. Daken StarkenbergCoe College | 6-0, 6-3 |
| Round of 128 | Tyler JohnsonGustavus Adolphus College def. Rob StorrickGrinnell College | 6-0, 6-1 |
| Round of 128 | Eric HilpeetWartburg College def. Allen-Michael MuenchUniversity of St. Thomas | 7-6 (7-1), 6-2 |
| Round of 128 | Florent MarcoUW-Eau Claire def. Matt JoostCarroll College | 6-1, 7-4 (7-4) |
| Round of 128 | Caleb RayLawrence University def. Derek HarringtonSt. Norbert College | 6-3, 6-3 |
| Round of 128 | L Peter StadumUW-La Crosse def. James MackSt. Scholastica | 7-5, 7-5 |
| Round of 128 | Grant LeisnerGustavus Adolphus College def. Jeff Damish1 | 6-1, 4-6, 10-5 |
| Round of 128 | Michael ColeGrinnell College def. Cam LaktashUW-Whitewater | 6-2, 6-3 |
| Round of 128 | Matt BellioLuther College def. Joe MeierUW-Eau Claire | 6-1, 7-5 |
| Round of 128 | Jon FossSt. Olaf College def. Brian RasmussenWartburg College | 6-2, 6-3 |
| Round of 128 | Evan ElderbrockMacalester def. Matt LobeckSt. Norbert College | 6-1, 6-2 |
| Round of 128 | Matt ZlevorLawrence University def. Martin DluhosGrinnell College | 6-4, 6-2 |
| Round of 128 | Andy CataniaSt. Olaf College def. Bradley EntwistleGustavus Adolphus College | 6-3, 1-6, 10-7 |
| Round of 128 | Jack MichaelCarroll College def. Vic MirasolaUW-La Crosse | 6-2, 6-4 |
| Round of 128 | Nick MozenaLuther College def. Dayton StevensWartburg College | 6-2, 6-1 |
| Round of 128 | Brain McCarthyUniversity of St. Thomas def. Michael JanssenCoe College | 6-1, 6-0 |
| Round of 128 | Michael RodenUW-Eau Claire def. Nick BoomgardenCarthage | 6-2, 6-4 |
| Round of 128 | Jason DunnLawrence University def. Nick AcostaSt. Norbert College | 6-0, 4-6, 10-5 |
| Round of 128 | Daniel PomerancGustavus Adolphus College def. John WrightSt. Olaf College | 6-3, 4-6, 10-6 |
| Round of 128 | Aaron LapkinGrinnell College def. Frankie GuiffreCarroll College | 6-2, 6-1 |
| Round of 128 | Michael WoolfCoe College def. DJ GrantWartburg College | 6-3, 6-1 |
| Round of 128 | Marcel GyswytGustavus Adolphus College def. Dan CooperUniversity of St. Thomas | 6-4, 6-4 |
| Round of 128 | James AyerLuther College def. Lewis WilcoxMacalester | 6-4, 6-3 |
| Round of 128 | Max SoghikianMacalester def. Andrew SheedyDenison | 6-3, 6-1 |
| Round of 128 | L Blayne WilladsenWartburg College def. Kevin HilpertSt. Scholastica | 6-4, 6-4 |
| Round of 128 | Ryan Vande LindeUW-Eau Claire def. Eric ScanlanUW-Whitewater | 6-3, 6-2 |
| Round of 128 | Aaron GendronLuther College def. Ian HansenSaint John's University | 2-6, 6-0, 10-5 |
| Round of 128 | Andrew HwangCarleton College def. Cody StrebigEdgewood College | 6-1, 6-4 |
| Round of 128 | Bernard MitamboHamline University def. Mitchell BlackeyUniversity of St. Thomas | 6-4, 6-4 |
| Round of 128 | John SilsethCarroll College def. Peter WrightUniversity of St. Thomas | 3-6, 6-4, 10-6 |
| Round of 128 | L Avery RuxCarleton College def. Jacob EngelstadSt. Scholastica | 6-0, 6-0 |
| Round of 128 | Elliot CzarneckiGrinnell College def. Charlie ReinertsenSt. Olaf College | 7-5, 6-3 |
| Round of 128 | Brian KleinUW-Whitewater def. Josh TruebloodWartburg College | 6-2, 6-0 |
| Round of 128 | Jonathan RogerCoe College def. Stephen TyndelMacalester | 7-6, 6-3 |
| Round of 128 | Alex McLeanCarthage def. Tim HartwickSt. Norbert College | 6-2, 6-4 |
| Round of 128 | Curtis NewmanCoe College def. Charlie WilhelmGrinnell College | 6-1, 6-0 |
| Round of 128 | Joey MacGibbonGustavus Adolphus College def. RJ RademacherUW-Whitewater | 6-4, 6-2 |
| Round of 128 | Robert BeckerHamline University def. Cooper SmithLawrence University | 6-2, 6-1 |
| Round of 128 | Mitch OsborneUW-Whitewater def. Chris BuckinghamWartburg College | 7-5, 6-2 |
| Round of 128 | W Dylan KellySt. Scholastica def. Eric SchneiderCarroll College | 6-1, 6-3 |
| Round of 64 | Amrik DonkenaGustavus Adolphus College def. Brady PorterUW-Whitewater | 6-2, 6-1 |
| Round of 64 | Knute GundersenSt. Olaf College def. Connor CunninghamGrinnell College | 6-1, 6-2 |
| Round of 64 | Victor KhristenkoCoe College def. Jon ArandaCarleton College | 0-6, 6-1, 7-6 |
| Round of 64 | Ethan NiquetUW-Whitewater def. Steven SkanseUniversity of St. Thomas | 6-0, 6-1 |
| Round of 64 | Daneric HazelmanCarthage def. Dan VollmmanCarleton College | 6-4, 7-6 |
| Round of 64 | Tyler JohnsonGustavus Adolphus College def. Allen-Michael MuenchUniversity of St. Thomas | 6-3, 6-2 |
| Round of 64 | Byron BalkinUW-Whitewater def. Florent MarcoUW-Eau Claire | 6-3, 6-4 |
| Round of 64 | Peter StadumUW-La Crosse def. Caleb RayLawrence University | 6-3, 6-4 |
| Round of 64 | Grant LeisnerGustavus Adolphus College def. Nicholas GarciaUniversity of Dubuque | 6-1, 4-6, 10-5 |
| Round of 64 | Michael ColeGrinnell College def. Joe MeierUW-Eau Claire | 4-6, 6-2, 10-7 |
| Round of 64 | Juan Luis ChuGustavus Adolphus College def. Jon FossSt. Olaf College | 6-0, 6-1 |
| Round of 64 | David CroonquistHamline University def. Evan ElderbrockMacalester | 6-4, 6-1 |
| Round of 64 | Martin DluhosGrinnell College def. Peter DunnCarleton College | 6-3, 6-0 |
| Round of 64 | Andy CataniaSt. Olaf College def. Jack MichaelCarroll College | 6-3, 6-0 |
| Round of 64 | Andrew BaylissUW-Whitewater def. Nick MozenaLuther College | 6-2, 6-1 |
| Round of 64 | Michael RodenUW-Eau Claire def. Brain McCarthyUniversity of St. Thomas | 6-2, 6-4 |
| Round of 64 | Daniel PomerancGustavus Adolphus College def. Jason DunnLawrence University | 6-3, 6-2 |
| Round of 64 | Aaron LapkinGrinnell College def. Andy McGlashenUW-Whitewater | 4-6, 6-3, 10-3 |
| Round of 64 | Marcel GyswytGustavus Adolphus College def. Michael WoolfCoe College | 6-1, 6-0 |
| Round of 64 | Jeff LotzCarthage def. James AyerLuther College | 6-3, 6-0 |
| Round of 64 | Max SoghikianMacalester def. Blayne WilladsenWartburg College | 6-7, 7-6, 10-5 |
| Round of 64 | Ryan Vande LindeUW-Eau Claire def. Noah SprinkelCoe College | 6-3, 6-3 |
| Round of 64 | Andrew HwangCarleton College def. Aaron GendronLuther College | 6-1, 6-4 |
| Round of 64 | Bernard MitamboHamline University def. Patrick ClarkGustavus Adolphus College | 3-6, 6-1, 10-7 |
| Round of 64 | Avery RuxCarleton College def. John SilsethCarroll College | 6-1, 6-0 |
| Round of 64 | Ramesh KarkiLuther College def. Elliot CzarneckiGrinnell College | 6-3, 0-6, 10-2 |
| Round of 64 | Mya Smith-DennisGustavus Adolphus College def. Brian KleinUW-Whitewater | 6-2, 6-3 |
| Round of 64 | Nick PiotrowskiUW-La Crosse def. Jonathan RogerCoe College | 6-2, 6-1 |
| Round of 64 | Curtis NewmanCoe College def. Alex McLeanCarthage | 7-5, 6-3 |
| Round of 64 | Fabricio MoncadaSaint John's University def. Joey MacGibbonGustavus Adolphus College | 4-6, 6-2, 10-4 |
| Round of 64 | Mitch OsborneUW-Whitewater def. Robert BeckerHamline University | 7-5, 6-3 |
| Round of 64 | L Chris KunaUW-Eau Claire def. Dylan KellySt. Scholastica | 6-0, 6-1 |
| Round of 32 | Amrik DonkenaGustavus Adolphus College def. Knute GundersenSt. Olaf College | 6-2, 6-1 |
| Round of 32 | Victor KhristenkoCoe College def. Ethan NiquetUW-Whitewater | 3-6, 6-4, 10-8 |
| Round of 32 | Tyler JohnsonGustavus Adolphus College def. Daneric HazelmanCarthage | 6-4, 7-5 |
| Round of 32 | Byron BalkinUW-Whitewater def. Peter StadumUW-La Crosse | 7-5, 6-3 |
| Round of 32 | Michael ColeGrinnell College def. Grant LeisnerGustavus Adolphus College | 4-6, 6-2, 10-7 |
| Round of 32 | David CroonquistHamline University def. Juan Luis ChuGustavus Adolphus College | 6-4, 6-7, 10-7 |
| Round of 32 | Andy CataniaSt. Olaf College def. Martin DluhosGrinnell College | 6-1, 6-0 |
| Round of 32 | Brain McCarthyUniversity of St. Thomas def. Andrew BaylissUW-Whitewater | 6-3, 6-2 |
| Round of 32 | Andy McGlashenUW-Whitewater def. Daniel PomerancGustavus Adolphus College | 6-2, 4-6, 10-8 |
| Round of 32 | Jeff LotzCarthage def. Marcel GyswytGustavus Adolphus College | 6-3, 6-7, 10-3 |
| Round of 32 | Ryan Vande LindeUW-Eau Claire def. Max SoghikianMacalester | 6-3, 6-3 |
| Round of 32 | Andrew HwangCarleton College def. Bernard MitamboHamline University | 6-3, 6-4 |
| Round of 32 | Ramesh KarkiLuther College def. Avery RuxCarleton College | 6-0, 6-3 |
| Round of 32 | Mya Smith-DennisGustavus Adolphus College def. Nick PiotrowskiUW-La Crosse | 2-6, 7-5, 10-7 |
| Round of 32 | Fabricio MoncadaSaint John's University def. Curtis NewmanCoe College | 7-5, 6-3 |
| Round of 32 | Chris KunaUW-Eau Claire def. Mitch OsborneUW-Whitewater | 3-6, 6-0, 11-9 |
| Round of 16 | Amrik DonkenaGustavus Adolphus College def. Victor KhristenkoCoe College | 6-3, 6-2 |
| Round of 16 | Byron BalkinUW-Whitewater def. Tyler JohnsonGustavus Adolphus College | 6-1, 4-6, 6-3 |
| Round of 16 | David CroonquistHamline University def. Grant LeisnerGustavus Adolphus College | 6-2, 6-2 |
| Round of 16 | Brain McCarthyUniversity of St. Thomas def. Andy CataniaSt. Olaf College | 6-3, 6-2 |
| Round of 16 | Jeff LotzCarthage def. Andy McGlashenUW-Whitewater | 4-6, 6-2, 6-1 |
| Round of 16 | Andrew HwangCarleton College def. Ryan Vande LindeUW-Eau Claire | 1-6, 6-1, 7-6 (7-4) |
| Round of 16 | Mya Smith-DennisGustavus Adolphus College def. Ramesh KarkiLuther College | 6-2, 6-3 |
| Round of 16 | Fabricio MoncadaSaint John's University def. Chris KunaUW-Eau Claire | 6-2, 6-4 |
| Quarterfinal | Amrik DonkenaGustavus Adolphus College def. Byron BalkinUW-Whitewater | 2-6, 7-6, 6-4 |
| Quarterfinal | Brain McCarthyUniversity of St. Thomas def. David CroonquistHamline University | 6-2, 6-3 |
| Quarterfinal | Jeff LotzCarthage def. Andrew HwangCarleton College | 6-1, 6-0 |
| Quarterfinal | Fabricio MoncadaSaint John's University def. Mya Smith-DennisGustavus Adolphus College | 1-6, 6-1, 6-2 |
| Semifinal | Amrik DonkenaGustavus Adolphus College def. Brain McCarthyUniversity of St. Thomas | 3-6, 6-4, 6-1 |
| Semifinal | Fabricio MoncadaSaint John's University def. Jeff LotzCarthage | 6-4, 2-6, 6-1 |
| Final | Amrik DonkenaGustavus Adolphus College def. Fabricio MoncadaSaint John's University | 7-5, 3-6, 6-4 |
