| Round of 128 | R. Rajshekar RamanUW-Whitewater def. Ben PratscherEdgewood College | 6-1, 6-0 |
| Round of 128 | Motasem Al-HouniGustavus Adolphus College def. Nathan TretsvenHamline University | 6-2, 6-2 |
| Round of 128 | Patton McClellandCarleton College def. Dayton StevensWartburg College | 6-2, 6-0 |
| Round of 128 | Alex BoomgardenCarthage def. Connor RustSaint John's University | 6-4, 6-3 |
| Round of 128 | Travis BuechelSt. Norbert College def. Jesse SchneebergerConcordia College | 7-6, 6-1 |
| Round of 128 | Matt BakerGustavus Adolphus College def. Matt SchullBethel University | 6-3, 6-4 |
| Round of 128 | Thomas PitcherGrinnell College def. Philip WierUniversity of St. Thomas | 6-2, 6-2 |
| Round of 128 | R. Burke AndersonUniversity of St. Thomas def. James AyerLuther College | 6-4, 1-6, 10-3 |
| Round of 128 | Brian KleinUW-Whitewater def. Patrick LagmanEdgewood College | 6-1, 6-3 |
| Round of 128 | Tim KahlCentral College def. Skip TurnerConcordia Wisconsin | 6-3, 6-1 |
| Round of 128 | Michael JanssenCoe College def. Alasdair McClinticMacalester College | 3-6, 6-4, 10-8 |
| Round of 128 | L Peter StadumUW-La Crosse def. Logan EngelstadSt. Scholastica | 6-3, 6-2 |
| Round of 128 | Cole MillerGrinnell College def. Collin KaczorowskiSaint Mary's University | 6-2, 6-1 |
| Round of 128 | Mitchell ElofsonGustavus Adolphus College def. Matt BisbeeUW-Whitewater | 6-7, 6-3, 10-3 |
| Round of 128 | Andrew HwangCarleton College def. Matt KavanaghUniversity of St. Thomas | 6-1, 6-1 |
| Round of 128 | Tracy JohnsonGrinnell College def. Chris ConleyCarthage | 6-2, 2-6, 10-4 |
| Round of 128 | Daniel EtmanUW-Whitewater def. Tyler AntilHamline University | 6-1, 6-1 |
| Round of 128 | W Josh StainerSt. Scholastica def. Chad MoklestadCoe College | 7-6, 6-4 |
| Round of 128 | Matt BulgerUW-La Crosse def. Johnny NygennCarroll College | 6-0, 6-0 |
| Round of 128 | L Kyle AppelLuther College def. Alex MihailovSt. Scholastica | 6-0, 6-2 |
| Round of 128 | Sean StokstadCoe College def. Brendan HollidgeUniversity of St. Thomas | 6-0, 6-2 |
| Round of 128 | Nick SkanavisUW-La Crosse def. Max SoghikianMacalester College | 6-0, 6-1 |
| Round of 128 | Kyle HoffmannUW-Eau Claire def. Samuel CatanzaroGrinnell College | 6-4, 6-4 |
| Round of 128 | Tony O'ConnellCarthage def. Michael WantaEdgewood College | 6-0, 6-0 |
| Round of 128 | Bryan MilesGustavus Adolphus College def. Tony O'ConnellCarthage | 6-1, 6-0 |
| Round of 128 | Koo MiyakeWartburg College def. Sawyer DargiewieczCarroll College | 6-1, 6-3 |
| Round of 128 | Yusuf ChowdhryLuther College def. Tony MirasolaUW-La Crosse | 2-6, 6-1, 10-2 |
| Round of 128 | W Nick LambrechtSt. Scholastica def. Steven SchullBethel University | 6-4, 6-2 |
| Round of 128 | Andres Saenz HoyoGustavus Adolphus College def. Austin PapenthienEdgewood College | 6-2, 6-2 |
| Round of 128 | Dylan SperryHamline University vs. Emilio GomezGrinnell College | 6-2, 1-6 |
| Round of 128 | Christian NagyCarleton College def. Steven SkanseUniversity of St. Thomas | 6-0, 6-3 |
| Round of 128 | Marcel GyswytGustavus Adolphus College def. Scott WallUniversity of St. Thomas | 6-2, 6-3 |
| Round of 128 | Torstein JystadLuther College def. Scott ButlerUW-Whitewater | 7-6, 6-4 |
| Round of 128 | Russell JohnsonConcordia Wisconsin def. Jack HansenSaint John's University | 7-6, 6-4 |
| Round of 128 | Ryan JumpCarthage def. Brian UtzMacalester College | 6-1, 6-4 |
| Round of 128 | West AdelmanCentral College def. Joey KronzerSt. Olaf College | 5-7, 6-4, 10-5 |
| Round of 128 | L Alex BerntCoe College def. Tiberiu CretuSt. Scholastica | 6-2, 6-2 |
| Round of 128 | Cam LaktashUW-Whitewater def. Rob StorrickGrinnell College | 6-0, 6-1 |
| Round of 128 | Ben CarlsonSt. Olaf College def. Nick StephanCarthage | 6-2, 6-2 |
| Round of 128 | Dante PiteraUW-La Crosse def. Alex HadjievEdgewood College | 6-2, 6-1 |
| Round of 128 | Logan PetersonGustavus Adolphus College def. Zack DeckerCoe College | 6-3, 5-7, 10-3 |
| Round of 128 | Eric HilpertWartburg College def. Tim HartwickSt. Norbert College | 7-6, 6-2 |
| Round of 128 | Matt BellioLuther College def. Derek LutzHamline University | 6-2, 6-3 |
| Round of 128 | Michael SchnarrUW-Whitewater def. Tom RundeUniversity of St. Thomas | 6-1, 6-7, 10-8 |
| Round of 128 | Stephen TyndelMacalester College def. Brian DavenportEdgewood College | 7-5, 6-2 |
| Round of 128 | L Isaiah MayerchakLuther College def. James MackSt. Scholastica | 6-2, 6-4 |
| Round of 128 | Pawel JaworskiCarthage def. Brady RademacherUniversity of St. Thomas | 6-2, 6-3 |
| Round of 128 | Steven WirtzSaint John's University def. Kirby RonningBethel University | 6-1, 6-0 |
| Round of 128 | Ryan HickmanCoe College def. Brayden ParmanUW-Eau Claire | 6-3, 6-4 |
| Round of 128 | Erik JohnsonCarleton College def. C.J. RayGrinnell College | 6-2, 6-3 |
| Round of 64 | Noah SprinkelCoe College def. R. Rajshekar RamanUW-Whitewater | 6-3, 6-3 |
| Round of 64 | Motasem Al-HouniGustavus Adolphus College def. Patton McClellandCarleton College | 6-2, 3-6, 10-6 |
| Round of 64 | Alex BoomgardenCarthage def. Travis BuechelSt. Norbert College | 6-0, 6-0 |
| Round of 64 | Thomas PitcherGrinnell College def. Matt BakerGustavus Adolphus College | 6-4, 1-6, 10-8 |
| Round of 64 | R. Burke AndersonUniversity of St. Thomas def. Grant LeisnerGustavus Adolphus College | 4-6, 6-2, 10-7 |
| Round of 64 | Brian KleinUW-Whitewater def. Tim KahlCentral College | 6-2, 6-2 |
| Round of 64 | Michael JanssenCoe College def. Ryan Vande LindeUW-Eau Claire | 6-4, 6-4 |
| Round of 64 | Cole MillerGrinnell College def. Peter StadumUW-La Crosse | 7-5, 7-5 |
| Round of 64 | Ramesh KarkiLuther College def. Mitchell ElofsonGustavus Adolphus College | 6-1, 6-2 |
| Round of 64 | Andrew HwangCarleton College def. Tracy JohnsonGrinnell College | 6-3, 6-0 |
| Round of 64 | Joe MacGibbonGustavus Adolphus College def. Daniel EtmanUW-Whitewater | 6-4, 6-0 |
| Round of 64 | L Matt BulgerUW-La Crosse def. Josh StainerSt. Scholastica | 6-3, 3-6, 11-9 |
| Round of 64 | Jake HumphreysUW-Whitewater def. Kyle AppelLuther College | 6-3, 1-6, 10-2 |
| Round of 64 | Sean StokstadCoe College def. Nick SkanavisUW-La Crosse | 6-3, 3-6, 10-4 |
| Round of 64 | Stephan NolanSt. Olaf College def. Kyle HoffmannUW-Eau Claire | 6-2, 6-2 |
| Round of 64 | Bryan MilesGustavus Adolphus College def. Tony O'ConnellCarthage | 6-0, 6-1 |
| Round of 64 | Yusuf ChowdhryLuther College def. Koo MiyakeWartburg College | 6-1, 6-3 |
| Round of 64 | L Riley GalbraithCoe College def. Nick LambrechtSt. Scholastica | 6-0, 6-2 |
| Round of 64 | Andres Saenz HoyoGustavus Adolphus College def. Emilio GomezGrinnell College | 6-2, 6-4 |
| Round of 64 | Byron BalkinUW-Whitewater def. Christian NagyCarleton College | 6-2, 6-1 |
| Round of 64 | Marcel GyswytGustavus Adolphus College def. Torstein JystadLuther College | 6-4, 6-3 |
| Round of 64 | Ryan JumpCarthage def. Erik JohnsonCarleton College | 6-7, 6-3, 10-5 |
| Round of 64 | Alex BerntCoe College def. West AdelmanCentral College | 6-0, 6-0 |
| Round of 64 | Mya Smith-DennisGustavus Adolphus College def. Cam LaktashUW-Whitewater | 6-3, 6-4 |
| Round of 64 | Ben CarlsonSt. Olaf College def. Dante PiteraUW-La Crosse | 1-6, 6-3, 10-8 |
| Round of 64 | Jack MichaelCarroll College def. Logan PetersonGustavus Adolphus College | 6-0, 6-1 |
| Round of 64 | Matt BellioLuther College def. Eric HilpertWartburg College | 6-1, 6-3 |
| Round of 64 | Juan Luis ChuGustavus Adolphus College def. Michael SchnarrUW-Whitewater | 7-5, 6-2 |
| Round of 64 | Isaiah MayerchakLuther College def. Stephen TyndelMacalester College | 6-4, 6-2 |
| Round of 64 | Brad EntwistleGustavus Adolphus College def. Pawel JaworskiCarthage | 6-2, 6-0 |
| Round of 64 | Ryan HickmanCoe College def. Steven WirtzSaint John's University | 6-0, 6-3 |
| Round of 64 | Ben ShklyarUW-Whitewater def. Erik JohnsonCarleton College | 4-6, retired |
| Round of 32 | Noah SprinkelCoe College def. Motasem Al-HouniGustavus Adolphus College | 6-1, 6-2 |
| Round of 32 | Alex BoomgardenCarthage def. Thomas PitcherGrinnell College | 1-0, 1-0 |
| Round of 32 | Brian KleinUW-Whitewater def. Grant LeisnerGustavus Adolphus College | 6-4, 6-3 |
| Round of 32 | Cole MillerGrinnell College def. Michael JanssenCoe College | 1-6, 6-3, 10-8 |
| Round of 32 | Ramesh KarkiLuther College def. Andrew HwangCarleton College | 1-0, 1-0 |
| Round of 32 | Joe MacGibbonGustavus Adolphus College def. Matt BulgerUW-La Crosse | 6-2, 6-0 |
| Round of 32 | Jake HumphreysUW-Whitewater def. Sean StokstadCoe College | 1-0, 1-0 |
| Round of 32 | Bryan MilesGustavus Adolphus College def. Stephan NolanSt. Olaf College | 6-0, 6-1 |
| Round of 32 | Riley GalbraithCoe College def. Yusuf ChowdhryLuther College | 6-1, 6-4 |
| Round of 32 | Byron BalkinUW-Whitewater def. Andres Saenz HoyoGustavus Adolphus College | 6-2, 6-4 |
| Round of 32 | Marcel GyswytGustavus Adolphus College def. Ryan JumpCarthage | 6-4, 6-4 |
| Round of 32 | Mya Smith-DennisGustavus Adolphus College def. Alex BerntCoe College | 6-3, 6-3 |
| Round of 32 | Jack MichaelCarroll College def. Ben CarlsonSt. Olaf College | 6-3, 6-0 |
| Round of 32 | Juan Luis ChuGustavus Adolphus College def. Matt BellioLuther College | 6-3, 6-3 |
| Round of 32 | Brad EntwistleGustavus Adolphus College def. Isaiah MayerchakLuther College | 6-1, 6-2 |
| Round of 32 | Ben ShklyarUW-Whitewater def. Ryan HickmanCoe College | 6-4, 3-6, 10-4 |
| Round of 16 | Noah SprinkelCoe College def. Alex BoomgardenCarthage | 6-7, 6-2, 6-3 |
| Round of 16 | Brian KleinUW-Whitewater def. Cole MillerGrinnell College | 6-2, 3-6, 6-1 |
| Round of 16 | Ramesh KarkiLuther College def. Joe MacGibbonGustavus Adolphus College | 6-3, 6-7, 6-4 |
| Round of 16 | Jake HumphreysUW-Whitewater def. Bryan MilesGustavus Adolphus College | 6-3, 6-0 |
| Round of 16 | Riley GalbraithCoe College def. Byron BalkinUW-Whitewater | 6-4, 6-4 |
| Round of 16 | Mya Smith-DennisGustavus Adolphus College def. Marcel GyswytGustavus Adolphus College | 6-0, 6-0 |
| Round of 16 | Jack MichaelCarroll College def. Juan Luis ChuGustavus Adolphus College | 6-4, 7-5 |
| Round of 16 | Ben ShklyarUW-Whitewater def. Brad EntwistleGustavus Adolphus College | 6-4, 3-6, 10-4 |
| Quarterfinal | Noah SprinkelCoe College def. Brian KleinUW-Whitewater | 5-7, 6-1, 6-1 |
| Quarterfinal | Jake HumphreysUW-Whitewater def. Ramesh KarkiLuther College | 6-1, 6-0 |
| Quarterfinal | Mya Smith-DennisGustavus Adolphus College def. Riley GalbraithCoe College | 6-4, 6-4 |
| Quarterfinal | Jack MichaelCarroll College def. Ben ShklyarUW-Whitewater | 6-3, 7-5 |
| Semifinal | Jake HumphreysUW-Whitewater def. Noah SprinkelCoe College | 6-0, 3-6, 6-3 |
| Semifinal | Jack MichaelCarroll College def. Mya Smith-DennisGustavus Adolphus College | 6-1, 6-2 |
| Final | Jake HumphreysUW-Whitewater def. Jack MichaelCarroll College | 5-7, 6-0, 6-2 |
