| Round of 128 | Chris ConleyCarthage def. Jaime BenavidesEdgewood College | 6-1, 6-1 |
| Round of 128 | Kolin KiekhoeferBethel University def. Mark KrollCoe College | 6-3, 6-3 |
| Round of 128 | Tim WolfordSaint Mary's University def. David YanagitaHamline | 6-3, 7-5 |
| Round of 128 | L Andrew NagelSaint John's University def. Tyler BatesSt. Scholastica | 6-4, 6-2 |
| Round of 128 | T. Connor ShivesGustavus Adolphus College def. Matt LindsayUW-La Crosse | 6-4, 6-4 |
| Round of 128 | Kyle HoffmannUW-Eau Claire def. Brad GuendelConcordia Wisconsin | 6-0, 6-1 |
| Round of 128 | Matt BulgerUW-La Crosse def. Luke PalmqusitBethel University | 6-3, 6-2 |
| Round of 128 | Martin BeckWisconsin-Whitewater def. Aidan TirpackMacalester College | 6-2, 6-4 |
| Round of 128 | Mauricio GonzalezCarelton College def. Austin PapenthienEdgewood College | 7-5, 7-6 (0-3) |
| Round of 128 | Peter JaegerCarroll University def. Matt KavanaghUniversity of St. Thomas | 6-3, 6-7 (0-4), 10-0 |
| Round of 128 | Andrew HwangCarelton College def. Leon GilmanSt. Norbert College | 6-0, 6-2 |
| Round of 128 | Issac ToivonenConcordia def. Matt BakerGustavus Adolphus College | 1-6, 7-6 (0-5), 10-8 |
| Round of 128 | Tommy SchubertUniversity of St. Thomas def. Matt MichaelCarroll University | 7-5, 6-3 |
| Round of 128 | L Tracy JohnsonGrinnel College def. Logan EngelstadSt. Scholastica | 2-6, 6-3, 10-3 |
| Round of 128 | Tim LarsonSaint John's University def. Nick SkanvisUW-La Crosse | 6-3, 6-0 |
| Round of 128 | Matt BisbeeWisconsin-Whitewater def. Ezra FrankelCarelton College | 6-4, 6-7 (3-0), 10-3 |
| Round of 128 | Brian DavenportEdgewood College def. Brant HeflinBethany Lutheran College | 6-4, 6-2 |
| Round of 128 | Brandon SchneiderUniversity of St. Thomas def. Charlie WilhelmGrinnel College | 6-7 (4-0), 7-6 (0-4), 10-5 |
| Round of 128 | W James MackSt. Scholastica def. Matt BettesGustavus Adolphus College | 6-1, 1-6, 10-8 |
| Round of 128 | Scott WallUniversity of St. Thomas def. Jacob KublerBethany Lutheran College | 6-0, 6-0 |
| Round of 128 | Isaiah MayerchakLuther College def. Joey KronzerSt. Olaf College | 6-4, 1-6, 10-5 |
| Round of 128 | Evan StoneEdgewood College def. Cody JahrigHamline | 6-1, 6-3 |
| Round of 128 | L Patton McClellandCarelton College def. Michael GobbelSt. Scholastica | 6-4, 6-3 |
| Round of 128 | Tommy EntwistleGustavus Adolphus College def. Dante PiteraUW-La Crosse | 6-4, 3-6, 10-4 |
| Round of 128 | W Josh StainerSt. Scholastica def. Quentin LamersCarroll University | 6-3, 6-2 |
| Round of 128 | Cam LaktashWisconsin-Whitewater def. Ben WaitUniversity of St. Thomas | 6-2, 0-6, 10-8 |
| Round of 128 | Cole MillerGrinnel College def. Tommy RundeUniversity of St. Thomas | 6-3, 6-2 |
| Round of 128 | Collin RiekeGustavus Adolphus College def. Michael WantaEdgewood College | 6-1, 6-1 |
| Round of 128 | Aaron LapkinGrinnel College def. Will WeyenbergUW-Eau Claire | 7-5, 6-3 |
| Round of 128 | Zach ZiturConcordia def. Steven WirtzSaint John's University | 7-6 (0-4), 6-1 |
| Round of 128 | Andres SaenzGustavus Adolphus College def. Nate GoszSt. Norbert College | 6-0, 6-1 |
| Round of 128 | Burke AndersonUniversity of St. Thomas def. Ben CarlsonSt. Olaf College | 6-3, 6-2 |
| Round of 128 | L Patrick LagmanEdgewood College def. Mike FontanaSt. Scholastica | 6-3, 6-7 (8-0), 10-8 |
| Round of 128 | Peter StadumUW-La Crosse def. Zach EcksteinGustavus Adolphus College | 6-4, 6-4 |
| Round of 128 | Tommy PitcherGrinnel College def. Brendan HollidgeUniversity of St. Thomas | 6-4, 7-5 |
| Round of 128 | Kevin MeiCarelton College def. Trent SchneiderLuther College | 1-0 |
| Round of 64 | Jake HumphreysWisconsin-Whitewater def. Chris ConleyCarthage | 6-4, 6-2 |
| Round of 64 | Tim WolfordSaint Mary's University def. Brady RadermacherUniversity of St. Thomas | 3-6, 6-0, 11-9 |
| Round of 64 | Bradley EntwistleGustavus Adolphus College def. Andrew NagelSaint John's University | 6-0, 6-0 |
| Round of 64 | Kyle HoffmannUW-Eau Claire def. Anthony MirasolaUW-La Crosse | 4-6, 7-6 (0-3), 10-4 |
| Round of 64 | Brady AndersonCoe College def. Matt BulgerUW-La Crosse | 6-7 (4-0), 6-1, 10-3 |
| Round of 64 | Emilio GomezGrinnel College def. Martin BeckWisconsin-Whitewater | 7-6 (0-4), 4-6, 10-6 |
| Round of 64 | Stephen NolanSt. Olaf College def. Mauricio GonzalezCarelton College | 7-6 (0-4), 6-1 |
| Round of 64 | Mitch ElofsonGustavus Adolphus College def. Peter JaegerCarroll University | 6-2, 6-1 |
| Round of 64 | Andrew HwangCarelton College def. Alex BoomgardenCarthage | 7-5, 6-2 |
| Round of 64 | Issac ToivonenConcordia def. Kolin KiekhoeferBethel University | 6-3, 6-1 |
| Round of 64 | Zane NavratilWisconsin-Whitewater def. Tommy SchubertUniversity of St. Thomas | 6-2, 6-3 |
| Round of 64 | Josh DoyleMacalester College def. Tracy JohnsonGrinnel College | 7-6 (0-5), 6-2 |
| Round of 64 | Motasem Al-HouniGustavus Adolphus College def. Tim LarsonSaint John's University | 6-2, 6-1 |
| Round of 64 | Alex BerntCoe College def. Brian DavenportEdgewood College | 6-2, 6-1 |
| Round of 64 | Kyle AppelLuther College def. Brandon SchneiderUniversity of St. Thomas | 6-1, 6-4 |
| Round of 64 | L Matt BisbeeWisconsin-Whitewater def. James MackSt. Scholastica | 4-6, 6-1, 10-5 |
| Round of 64 | T. Connor ShivesGustavus Adolphus College def. Scott WallUniversity of St. Thomas | 4-6, 6-1, 10-3 |
| Round of 64 | Elliot CzarneckiGrinnel College def. Isaiah MayerchakLuther College | 6-0, 6-3 |
| Round of 64 | R. Rajshekhar RamanWisconsin-Whitewater def. Evan StoneEdgewood College | 6-0, 6-3 |
| Round of 64 | Mohanad Al HouniGustavus Adolphus College def. Patton McClellandCarelton College | 6-2, 6-1 |
| Round of 64 | Ryan JumpCarthage def. Tommy EntwistleGustavus Adolphus College | 6-2, 6-4 |
| Round of 64 | W Josh StainerSt. Scholastica def. Erik JohnsonCarelton College | 2-6, 6-3, 11-9 |
| Round of 64 | Jack HansenSaint John's University def. Cam LaktashWisconsin-Whitewater | 2-6, 7-5, 10-7 |
| Round of 64 | Riley GalbraithCoe College def. Cole MillerGrinnel College | 6-2, 6-2 |
| Round of 64 | Brian UtzMacalester College def. Collin RiekeGustavus Adolphus College | 6-2, 6-2 |
| Round of 64 | Aaron LapkinGrinnel College def. Matt SchullBethel University | 6-1, 5-7, 10-2 |
| Round of 64 | Andres SaenzGustavus Adolphus College def. Zach ZiturConcordia | 6-1, 6-1 |
| Round of 64 | Ben ShklyarWisconsin-Whitewater def. Burke AndersonUniversity of St. Thomas | 6-1, 6-1 |
| Round of 64 | Jordan VerbauwhedeCarthage def. Patrick LagmanEdgewood College | 6-1, 6-4 |
| Round of 64 | Ryan HickmanCoe College def. Peter StadumUW-La Crosse | 6-1, 6-7 (2-0), 10-2 |
| Round of 64 | Tommy PitcherGrinnel College def. Michael SchnarrWisconsin-Whitewater | 7-6 (0-3), 7-5 |
| Round of 64 | Jack MichaelCarroll University def. Kevin MeiCarelton College | 6-3, 6-3 |
| Round of 32 | Jake HumphreysWisconsin-Whitewater def. Tim WolfordSaint Mary's University | 6-0, 6-1 |
| Round of 32 | Bradley EntwistleGustavus Adolphus College def. Kyle HoffmannUW-Eau Claire | 6-1, 6-1 |
| Round of 32 | Brady AndersonCoe College def. Emilio GomezGrinnel College | 7-5, 6-1 |
| Round of 32 | Mitch ElofsonGustavus Adolphus College def. Stephen NolanSt. Olaf College | 6-2, 7-5 |
| Round of 32 | Issac ToivonenConcordia def. Andrew HwangCarelton College | 6-3, 6-4 |
| Round of 32 | Josh DoyleMacalester College def. Zane NavratilWisconsin-Whitewater | 4-6, 7-6, 13-11 |
| Round of 32 | Motasem Al-HouniGustavus Adolphus College def. Alex BerntCoe College | 6-2, 6-0 |
| Round of 32 | Matt BisbeeWisconsin-Whitewater def. Kyle AppelLuther College | 6-1, 6-1 |
| Round of 32 | Elliot CzarneckiGrinnel College def. T. Connor ShivesGustavus Adolphus College | 3-6, 6-1, 11-9 |
| Round of 32 | Mohanad Al HouniGustavus Adolphus College def. R. Rajshekhar RamanWisconsin-Whitewater | 6-1, 6-2 |
| Round of 32 | L Ryan JumpCarthage def. Josh StainerSt. Scholastica | 6-2, 6-2 |
| Round of 32 | Jack HansenSaint John's University def. Riley GalbraithCoe College | 6-3, 7-5 |
| Round of 32 | Brian UtzMacalester College def. Aaron LapkinGrinnel College | 3-6, 6-1, 10-4 |
| Round of 32 | Andres SaenzGustavus Adolphus College def. Ben ShklyarWisconsin-Whitewater | 6-3, 6-3 |
| Round of 32 | Ryan HickmanCoe College def. Jordan VerbauwhedeCarthage | 6-2, 6-4 |
| Round of 32 | Jack MichaelCarroll University def. Tommy PitcherGrinnel College | 6-1, 6-1 |
| Round of 16 | Bradley EntwistleGustavus Adolphus College def. Jake HumphreysWisconsin-Whitewater | 6-4, 6-4 |
| Round of 16 | Brady AndersonCoe College def. Mitch ElofsonGustavus Adolphus College | 6-3, 6-4 |
| Round of 16 | Issac ToivonenConcordia def. Josh DoyleMacalester College | 6-3, 6-1 |
| Round of 16 | Motasem Al-HouniGustavus Adolphus College def. Matt BisbeeWisconsin-Whitewater | 6-1, 6-3 |
| Round of 16 | Mohanad Al HouniGustavus Adolphus College def. Elliot CzarneckiGrinnel College | 7-5, 6-0 |
| Round of 16 | Ryan JumpCarthage def. Jack HansenSaint John's University | 6-4, 6-2 |
| Round of 16 | Andres SaenzGustavus Adolphus College def. Brian UtzMacalester College | 6-3, 6-3 |
| Round of 16 | Jack MichaelCarroll University def. Ryan HickmanCoe College | 6-3, 6-2 |
| Quarterfinal | Bradley EntwistleGustavus Adolphus College def. Brady AndersonCoe College | 6-4, 6-4 |
| Quarterfinal | Motasem Al-HouniGustavus Adolphus College def. Issac ToivonenConcordia | 4-6, 6-0, 6-1 |
| Quarterfinal | Mohanad Al HouniGustavus Adolphus College def. Ryan JumpCarthage | 6-1, 6-2 |
| Quarterfinal | Jack MichaelCarroll University def. Andres SaenzGustavus Adolphus College | 6-3, 6-4 |
| Semifinal | Motasem Al-HouniGustavus Adolphus College def. Bradley EntwistleGustavus Adolphus College | 6-4, 2-6, 6-2 |
| Semifinal | Mohanad Al HouniGustavus Adolphus College def. Jack MichaelCarroll University | 6-2, 7-5 |
| Final | Motasem Al-HouniGustavus Adolphus College def. Mohanad Al HouniGustavus Adolphus College | 7-5, 6-4 |
