| Round of 128 | Juan Carlos PerezGrinnell College def. BYE | by default |
| Round of 128 | L Mitch BlackeyUniversity of St. Thomas def. Brendan AndersonSt. Scholastica | 6-2, 6-1 |
| Round of 128 | Joey MacGibbonGustavus Adolphus College def. Charlie MillerUW-Whitewater | 7-6, 6-0 |
| Round of 128 | Kyle TuckerCoe College def. Max ZlevorLawrence University | 7-5, 6-2 |
| Round of 128 | Ramesh KarkiLuther College def. Chris FowlerMacalester College | 6-2, 6-3 |
| Round of 128 | Ethan NiquetUW-Whitewater def. Kent NicholsBethel University | 7-5, 6-2 |
| Round of 128 | Chris BuckinghamWartburg College def. Matt ZellnerCarroll College | 6-2, 6-0 |
| Round of 128 | Derek HarringtonSt. Norbert College def. Matt EdinConcordia College | 6-7, 7-6, 10-8 |
| Round of 128 | Tyler JohnsonGustavus Adolphus College def. Lewis WilcoxMacalester College | 6-1, 6-2 |
| Round of 128 | L Brian TresedderConcordia University def. Tucker CombsSt. Scholastica | 6-1, 6-4 |
| Round of 128 | Eric WollumUW- Eau Claire def. Curtis NewmanCoe College | 7-5, 6-0 |
| Round of 128 | Ian HansenSaint John's University def. Demetrius JohnsonUniversity of Dubuque | 7-6, 6-3 |
| Round of 128 | Henry MandellUniversity of St. Thomas def. Daniel NellisGrinnell College | 6-0, 6-1 |
| Round of 128 | Aaron GendronLuther College def. Robert GroenCarleton College | 6-3, 6-3 |
| Round of 128 | Robert BeckerHamline University vs. Steve QuiringUW-La Crosse | no result |
| Round of 128 | Jake MaceyUW-Whitewater def. BYE | by default |
| Round of 128 | Chris KunaEdgewood College def. BYE | by default |
| Round of 128 | Bernard MitamboHamline University def. Matt JoostCarroll College | 6-0, 6-2 |
| Round of 128 | Byron BalkinUW-Whitewater def. Mike LunkaSaint Mary's University | 6-3, 6-2 |
| Round of 128 | Jonathan RogerCoe College def. Paul MairetMacalester College | 6-2, 6-1 |
| Round of 128 | Roy WimerLawrence University def. Andy MichelsUniversity of St. Thomas | 6-0, 6-1 |
| Round of 128 | Dayton StevensWartburg College def. Bolun ZhangGrinnell College | 6-1, 6-0 |
| Round of 128 | L Juan Luis ChuGustavus Adolphus College def. Dylan KellySt. Scholastica | 6-1, 6-0 |
| Round of 128 | Austin JiangCarleton College def. BYE | by default |
| Round of 128 | Jeff LotzCarthage College def. Matt BellioLuther College | 6-4, 6-4 |
| Round of 128 | Colin JohnsonGrinnell College def. Rodrigo OteroGustavus Adolphus College | 7-6, 6-2 |
| Round of 128 | Knute GundersenSt. Olaf College def. Ryan Van De LindeLawrence University | 6-1, 3-6, 10-5 |
| Round of 128 | Paul CooperCarleton College def. Nic SchultzCarroll College | 6-1, 6-1 |
| Round of 128 | Scott StegemannCoe College def. Peter WrightUniversity of St. Thomas | 0-6, 6-3, 10-3 |
| Round of 128 | Brian OlsonConcordia College def. Tim HartwickSt. Norbert College | 7-6, 6-3 |
| Round of 128 | Grant LeisnerGustavus Adolphus College def. Erik ScanlanUW-Whitewater | 6-4, 6-3 |
| Round of 128 | Harry WhiteleyLuther College def. BYE | by default |
| Round of 128 | Scott SundstromLuther College def. BYE | by default |
| Round of 128 | Bryan MilesGustavus Adolphus College def. Max EdwardsMacalester College | 6-4, 6-4 |
| Round of 128 | Andy McGlashenUW-Whitewater def. Anthony GrecoWartburg College | 6-0, 6-1 |
| Round of 128 | Ben FlebbeGrinnell College def. Sam ScheevelBethel University | 7-6, 6-4 |
| Round of 128 | Pat SchramkaConcordia University def. Matt BergstromUniversity of St. Thomas | 1-6, 6-1, 10-4 |
| Round of 128 | Alex ChinCarleton College def. Bud FeketeUW-La Crosse | 6-2, 6-1 |
| Round of 128 | John WightSt. Olaf College def. Michael JanssenCoe College | 6-1, 6-2 |
| Round of 128 | Fabricio MoncadaSaint John's University def. Dan BowserCentral College | 6-3, 6-3 |
| Round of 128 | Nick GarciaUniversity of Dubuque def. BYE | by default |
| Round of 128 | Brankie GiuffreCarroll College def. Josh SweereSt. Norbert College | 6-3, 6-1 |
| Round of 128 | L Marcel GyswytGustavus Adolphus College def. Jacob EngelstadSt. Scholastica | 6-2, 6-2 |
| Round of 128 | Kevin WalkerUniversity of St. Thomas def. James AyerLuther College | 6-1, 6-1 |
| Round of 128 | Nick BoomgardenCarthage College def. Victor KhristenkoCoe College | 6-2, 6-2 |
| Round of 128 | Jason DunnLawrence University def. Connor HartHamline University | 6-0, 6-0 |
| Round of 128 | Mitch OsborneUW-Whitewater def. Ishan BhadkamkarGrinnell College | 6-0, 6-2 |
| Round of 128 | Lars OlsonUW- Eau Claire def. Brooks StapletonGustavus Adolphus College | 6-2, 7-5 |
| Round of 128 | Daneric HazelmanCarthage College def. BYE | by default |
| Round of 128 | Samriddh BurmanLuther College def. Brady PorterUW-Whitewater | 6-0, 6-0 |
| Round of 128 | Brendan O'ConnellUniversity of St. Thomas def. Chad SmithConcordia College | 6-2, 6-3 |
| Round of 128 | Kevin RasmussenCarroll College def. Ali BandealiMacalester College | 6-4, 6-0 |
| Round of 128 | David CroonquistHamline University def. Matthew LobeckSt. Norbert College | 6-0, 6-1 |
| Round of 128 | Daniel PomerancGustavus Adolphus College def. Martin DluhosGrinnell College | 6-0, 6-2 |
| Round of 128 | Max PiepkornLuther College def. Sean StokstadCoe College | 0-6, 7-5, 10-5 |
| Round of 128 | Andrew BaylissUW-Whitewater def. Brian RasmussenWartburg College | 6-2, 6-0 |
| Round of 128 | Dmitriy GlumovGrinnell College def. Tyler Van HeestLuther College | 6-0, 6-0 |
| Round of 128 | Nick PiotrowskiUW-La Crosse def. Jeff DamishCoe College | 6-2, 7-6 |
| Round of 128 | Kyle HelgemoeHamline University def. John D'OrazioEdgewood College | 6-1, 6-0 |
| Round of 128 | Michael ColemanMacalester College def. Dan VollmanCarleton College | 6-1, 6-2 |
| Round of 128 | Peter MohrLawrence University def. Tucker MorrisBethel University | by default |
| Round of 128 | L Devin LarsonConcordia College def. Kevin HilpertSt. Scholastica | 7-6, 3-6, 1-0 (10-7) |
| Round of 128 | Nicholas MozenaLuther College vs. Will KriegerUW-Whitewater | no result |
| Round of 128 | Amrik DonkenaGustavus Adolphus College def. BYE | by default |
| Round of 64 | Juan Carlos PerezGrinnell College def. Mitch BlackeyUniversity of St. Thomas | 6-1, 6-1 |
| Round of 64 | Joey MacGibbonGustavus Adolphus College def. Kyle TuckerCoe College | 6-2, 6-2 |
| Round of 64 | Ethan NiquetUW-Whitewater def. Ramesh KarkiLuther College | 6-3, 3-6, 10-8 |
| Round of 64 | Derek HarringtonSt. Norbert College def. Chris BuckinghamWartburg College | 6-3, 7-5 |
| Round of 64 | Tyler JohnsonGustavus Adolphus College def. Brian TresedderConcordia University | 6-4, 6-3 |
| Round of 64 | Ian HansenSaint John's University def. Eric WollumUW- Eau Claire | 6-4, 6-2 |
| Round of 64 | Aaron GendronLuther College def. Henry MandellUniversity of St. Thomas | 6-1, 6-3 |
| Round of 64 | Jake MaceyUW-Whitewater def. Robert BeckerHamline University | 6-0, 6-0 |
| Round of 64 | Chris KunaEdgewood College def. Bernard MitamboHamline University | 6-4, 6-2 |
| Round of 64 | Byron BalkinUW-Whitewater def. Jonathan RogerCoe College | 6-4, 2-0, retired |
| Round of 64 | Bolun ZhangGrinnell College def. Roy WimerLawrence University | 6-3, 6-2 |
| Round of 64 | Juan Luis ChuGustavus Adolphus College def. Austin JiangCarleton College | 7-5, 6-1 |
| Round of 64 | Jeff LotzCarthage College def. Colin JohnsonGrinnell College | 6-4, 6-2 |
| Round of 64 | Paul CooperCarleton College def. Knute GundersenSt. Olaf College | 6-3, 7-6 (7-5) |
| Round of 64 | Scott StegemannCoe College def. Brian OlsonConcordia College | 6-1, 6-2 |
| Round of 64 | Harry WhiteleyLuther College def. Grant LeisnerGustavus Adolphus College | 6-4, 6-3 |
| Round of 64 | Scott SundstromLuther College def. Bryan MilesGustavus Adolphus College | 6-4, 6-1 |
| Round of 64 | Andy McGlashenUW-Whitewater def. Ben FlebbeGrinnell College | 6-3, 6-3 |
| Round of 64 | Alex ChinCarleton College def. Pat SchramkaConcordia University | 6-4, 6-3 |
| Round of 64 | Fabricio MoncadaSaint John's University def. John WightSt. Olaf College | 7-5, 6-1 |
| Round of 64 | Nick GarciaUniversity of Dubuque def. Brankie GiuffreCarroll College | 6-2, 6-1 |
| Round of 64 | Marcel GyswytGustavus Adolphus College def. Kevin WalkerUniversity of St. Thomas | 7-5, 6-2 |
| Round of 64 | Victor KhristenkoCoe College def. Jason DunnLawrence University | 7-6, 6-3 |
| Round of 64 | Mitch OsborneUW-Whitewater def. Lars OlsonUW- Eau Claire | 6-4, 7-5 |
| Round of 64 | Daneric HazelmanCarthage College def. Samriddh BurmanLuther College | 7-6, 6-3 |
| Round of 64 | Brendan O'ConnellUniversity of St. Thomas def. Kevin RasmussenCarroll College | 6-2, 6-1 |
| Round of 64 | Daniel PomerancGustavus Adolphus College def. David CroonquistHamline University | 7-5, 6-1 |
| Round of 64 | Andrew BaylissUW-Whitewater def. Max PiepkornLuther College | 6-2, 6-1 |
| Round of 64 | Nick PiotrowskiUW-La Crosse vs. Dmitriy GlumovGrinnell College | no result |
| Round of 64 | Michael ColemanMacalester College vs. Kyle HelgemoeHamline University | no result |
| Round of 64 | Tucker MorrisBethel University def. Devin LarsonConcordia College | 6-2, 6-3 |
| Round of 64 | Amrik DonkenaGustavus Adolphus College def. Will KriegerUW-Whitewater | 6-4, 2-6, 10-6 |
| Round of 32 | Juan Carlos PerezGrinnell College def. Joey MacGibbonGustavus Adolphus College | 6-0, 7-6 (7-4) |
| Round of 32 | Ethan NiquetUW-Whitewater def. Derek HarringtonSt. Norbert College | 6-4, 6-0 |
| Round of 32 | Tyler JohnsonGustavus Adolphus College def. Ian HansenSaint John's University | 2-6, 6-1, 10-4 |
| Round of 32 | Jake MaceyUW-Whitewater def. Aaron GendronLuther College | 6-2, 6-3 |
| Round of 32 | Byron BalkinUW-Whitewater def. Chris KunaEdgewood College | 6-4, 4-6, 10-3 |
| Round of 32 | Bolun ZhangGrinnell College def. Juan Luis ChuGustavus Adolphus College | 2-6, 6-3, 10-3 |
| Round of 32 | Paul CooperCarleton College def. Jeff LotzCarthage College | 2-6, 6-4, 10-8 |
| Round of 32 | Scott StegemannCoe College def. Harry WhiteleyLuther College | 6-3, 3-6, 10-8 |
| Round of 32 | Scott SundstromLuther College def. Andy McGlashenUW-Whitewater | 6-2, 6-2 |
| Round of 32 | Fabricio MoncadaSaint John's University def. Alex ChinCarleton College | 6-7, 6-0, 10-6 |
| Round of 32 | Nick GarciaUniversity of Dubuque def. Marcel GyswytGustavus Adolphus College | 7-6 (7-5), 3-6, 10-5 |
| Round of 32 | Victor KhristenkoCoe College def. Mitch OsborneUW-Whitewater | 6-4, 3-0, retired |
| Round of 32 | Daneric HazelmanCarthage College def. Brendan O'ConnellUniversity of St. Thomas | 7-6 (7-4), 4-6, 10-7 |
| Round of 32 | Andrew BaylissUW-Whitewater def. Daniel PomerancGustavus Adolphus College | 7-6, 2-6, 11-9 |
| Round of 32 | Nick PiotrowskiUW-La Crosse def. Michael ColemanMacalester College | 6-4, 6-1 |
| Round of 32 | Amrik DonkenaGustavus Adolphus College def. Tucker MorrisBethel University | 6-2, 6-2 |
| Round of 16 | Juan Carlos PerezGrinnell College def. Ethan NiquetUW-Whitewater | 6-2, 6-2 |
| Round of 16 | Jake MaceyUW-Whitewater def. Tyler JohnsonGustavus Adolphus College | 6-1, 6-2 |
| Round of 16 | Byron BalkinUW-Whitewater def. Bolun ZhangGrinnell College | 6-3, 6-3 |
| Round of 16 | Scott StegemannCoe College def. Paul CooperCarleton College | 6-2, 4-6, 7-6 (8-6) |
| Round of 16 | Scott SundstromLuther College def. Fabricio MoncadaSaint John's University | 6-7, 6-0, 10-6 |
| Round of 16 | Nick GarciaUniversity of Dubuque def. Victor KhristenkoCoe College | 6-2, 6-4 |
| Round of 16 | Daneric HazelmanCarthage College def. Andrew BaylissUW-Whitewater | 6-4, 6-3 |
| Round of 16 | Amrik DonkenaGustavus Adolphus College def. Nick PiotrowskiUW-La Crosse | 6-3, 6-2 |
| Quarterfinal | Juan Carlos PerezGrinnell College def. Jake MaceyUW-Whitewater | 7-5, 6-7 (9-11), 6-3 |
| Quarterfinal | Byron BalkinUW-Whitewater def. Scott StegemannCoe College | 5-7, 6-0, 6-3 |
| Quarterfinal | Nick GarciaUniversity of Dubuque def. Scott SundstromLuther College | 6-2, 6-3 |
| Quarterfinal | Amrik DonkenaGustavus Adolphus College def. Daneric HazelmanCarthage College | 6-3, 6-2 |
| Semifinal | Byron BalkinUW-Whitewater def. Juan Carlos PerezGrinnell College | 6-4, 6-4 |
| Semifinal | Nick GarciaUniversity of Dubuque def. Amrik DonkenaGustavus Adolphus College | 6-3, 6-4 |
| Final | Nick GarciaUniversity of Dubuque def. Byron BalkinUW-Whitewater | 6-1, 6-1 |
| Consolation | L Demetrius JohnsonUniversity of Dubuque def. Tucker CombsSt. Scholastica | 8-6 |
| Consolation | L Nicholas MozenaLuther College def. Dylan KellySt. Scholastica | 8-3 |
| Consolation | L Grant LeisnerGustavus Adolphus College def. Kolin DeanSt. Scholastica | 8-4 |
| Consolation | L Ishan BhadkamkarGrinnell College def. Brendan AndersonSt. Scholastica | 8-3 |
| Consolation | L Matthew LobeckSt. Norbert College def. Nick LindSt. Scholastica | 8-6 |
| Consolation | L Tyler Van HeestLuther College def. Brian LindbergSt. Scholastica | 8-1 |
| Consolation | W Jacob EngelstadSt. Scholastica def. Sam ScheevelBethel University | 8-4 |
| Consolation | L Skip TurnerConcordia University def. Mike AroSt. Scholastica | 8-2 |
| Consolation | W Jacob EngelstadSt. Scholastica def. Roy WimerLawrence University | 8-0 |
| Consolation | L Brian RasmussenWartburg College def. Jacob EngelstadSt. Scholastica | 8-5 |