| Round of 128 | Brandon KuetherHamline University def. Nicholas AlexGrinnell College | 7-5, 6-2 |
| Round of 128 | Dexter JacksonBethany Lutheran def. Connor SchanenCornell College | 6-0, 6-3 |
| Round of 128 | Sam NettletonWartburg def. Gabe BinversieConcordia Wisconsin | 6-3, 6-1 |
| Round of 128 | Matt DurhamUW-Eau Claire def. Steven LeeBethel University | 6-2, 5-7, 11-9 |
| Round of 128 | Brady HicksSt. Norbert College def. Brendan LonderganLuther College | 6-3, 6-2 |
| Round of 128 | Jonas Lindholm-UzziCarleton College def. Jordan PieperNebraska Wesleyan | 6-1, 6-0 |
| Round of 128 | Tate HovlandConcordia Moorhead def. Paul StewartSaint Mary's University | 6-0, 6-0 |
| Round of 128 | Alex SenjemGustavus Adolphus College def. Arlo DetmerGrinnell College | 6-4, 6-3 |
| Round of 128 | Ben WilsonMacalester def. Christian YunSt. Olaf | 6-2, 6-1 |
| Round of 128 | Tim FifarekSt. Norbert College def. Riley PetersonUW-La Crosse | 6-0, 6-1 |
| Round of 128 | W Bryce GadkeSt. Scholastica def. Tom PrittinenSaint John's University | 6-3, 6-0 |
| Round of 128 | Connor MaloneyLawrence University def. Scott SchwandtConcordia Moorhead | 6-1, 6-2 |
| Round of 128 | Tom GreeneCornell College def. Alex HolmSaint Mary's University | 6-2, 6-3 |
| Round of 128 | Derek WilliamsNorthwestern (Minn.) def. Andrew NemcekCarroll | 6-1, 7-6 |
| Round of 128 | Adam OlsonNebraska Wesleyan def. Gus Fedje-JohnstonSt. Olaf | 6-2, 6-0 |
| Round of 128 | Morgan RossCarleton College def. Kieran TownsendGustavus Adolphus College | 6-0, 6-0 |
| Round of 128 | Cam LongLuther College def. Blake KuetherHamline University | 6-1, 6-1 |
| Round of 128 | Zach KnudsenUW-Eau Claire def. Kyle SwansonSaint Mary's University | 6-2, 6-1 |
| Round of 128 | Lucas LeDouxGrinnell College def. Cameron FairNorthwestern (Minn.) | 6-1, 7-5 |
| Round of 128 | Michael LockhartMacalester def. Corey DuncanCornell College | 7-5, 6-3 |
| Round of 128 | L Ben McKimmSaint John's University def. Zach MeikleSt. Scholastica | 6-0, 6-0 |
| Round of 128 | Jared ScherlingNebraska Wesleyan def. Dalton WerckmanBethany Lutheran | 4-6, 6-4, 10-6 |
| Round of 128 | Jacob EndresGustavus Adolphus College def. Jordan CrumpSt. Norbert College | 6-1, 6-1 |
| Round of 128 | Charlie ParishUW-La Crosse def. Carter LinderHamline University | 6-2, 6-1 |
| Round of 128 | Henry MorrisBethel University def. John ZanottiSt. Norbert College | 6-1, 6-4 |
| Round of 128 | Aditya VasavanSt. Olaf def. Nathan RaskinConcordia Wisconsin | 6-2, 4-6, 10-6 |
| Round of 128 | Jeremy EllerbyWartburg def. Alex RandCornell College | 6-1, 6-4 |
| Round of 128 | Laine LarsonBethany Lutheran def. Carter SteffesConcordia Moorhead | 6-4, 6-0 |
| Round of 128 | Nick Van Den HandleCornell College def. Christian CannonNebraska Wesleyan | 6-2, 6-1 |
| Round of 128 | Jess HansenSaint John's University def. Kahlo VueSt. Norbert College | 6-0, 6-1 |
| Round of 128 | CJ CliffCentral College def. Bobby TiedemanSaint Mary's University | 6-4, 6-2 |
| Round of 128 | L Mitchel GjersethCarroll def. Jason KentSt. Scholastica | 6-1, 6-7, 17-15 |
| Round of 128 | Nick KnudsonBethel University def. Corey LokenSt. Olaf | 3-6, 6-0, 10-7 |
| Round of 128 | Landon RidpathNorthwestern (Minn.) def. Izaya TurenneLawrence University | 6-0, 6-2 |
| Round of 128 | Nathan KnappConcordia Wisconsin def. Ryan KuceraLuther College | 6-1, 1-6, 10-8 |
| Round of 128 | Jesse SchneebergerConcordia Moorhead def. Caleb PerkinsBethel University | 6-2, 6-0 |
| Round of 128 | Christian PurnellCarleton College def. Jordan PoffBethany Lutheran | 6-0, 6-0 |
| Round of 128 | Ben KlimekHamline University def. John LunnGrinnell College | 6-2, 7-6, 11-9 |
| Round of 128 | Zeke HaugenGustavus Adolphus College def. Luke AndrekusSt. Norbert College | 6-1, 6-1 |
| Round of 128 | Joey ShubertUW-La Crosse def. Hale BreitNebraska Wesleyan | 6-1, 6-3 |
| Round of 128 | Raghuram InturiGrinnell College def. Matt La VioletteSt. Norbert College | 6-1, 6-2 |
| Round of 128 | Corey PenickHamline University def. Allessandro MauceriMacalester | 6-4, 6-3 |
| Round of 128 | Zach JanssenUW-Eau Claire def. Nathan AbbottLuther College | 6-1, 6-0 |
| Round of 128 | Alex ZuzekSaint Mary's University def. Auston SackCornell College | 6-1, 6-3 |
| Round of 128 | Tommy WillarUW-La Crosse def. G. UnnikrishnanSt. Olaf | 6-2, 6-0 |
| Round of 128 | Andrew SharngCarleton College def. Can-Aras ThierhoffGustavus Adolphus College | 6-2, 6-0 |
| Round of 128 | Matthew EngumConcordia Moorhead def. Carter DahlBethany Lutheran | 6-4, 6-1 |
| Round of 128 | Christopher ProkoschSt. Olaf def. Grahamm KelloggGustavus Adolphus College | 6-4, 6-1 |
| Round of 128 | Lewis WhiteCarleton College def. Jace MantheHamline University | 6-0, 6-2 |
| Round of 128 | Kenny GoinsLuther College def. Dylan MannetterUW-La Crosse | 6-4, 6-2 |
| Round of 128 | Peter LindbergBethel University def. Jarod SwobodaSaint John's University | 6-4, 6-0 |
| Round of 128 | Joe OleniczakSt. Norbert College def. Hiro HaradoCornell College | 6-3, 6-3 |
| Round of 128 | Trevor BudewitzConcordia Wisconsin def. JT RottinghausWartburg | 6-4, 6-1 |
| Round of 128 | W Zach StrawSt. Scholastica def. Cade FrancourLawrence University | 6-4, 6-2 |
| Round of 64 | Brandon KuetherHamline University def. Jacob HuntoonEdgewood College | 6-0, 6-1 |
| Round of 64 | Sam NettletonWartburg def. Dexter JacksonBethany Lutheran | 6-0, 6-0 |
| Round of 64 | Brady HicksSt. Norbert College def. Matt DurhamUW-Eau Claire | 6-3, 6-1, 10-8 |
| Round of 64 | Tate HovlandConcordia Moorhead def. Jonas Lindholm-UzziCarleton College | 6-0, 6-0 |
| Round of 64 | Alex SenjemGustavus Adolphus College def. Andrew JelkenBethany Lutheran | 7-5, 6-0 |
| Round of 64 | Riley PetersonUW-La Crosse def. Ben WilsonMacalester | 6-4, 6-1, 10-8 |
| Round of 64 | W Bryce GadkeSt. Scholastica def. Connor MaloneyLawrence University | 6-4, 6-3 |
| Round of 64 | Derek WilliamsNorthwestern (Minn.) def. Tom GreeneCornell College | 6-4, 6-2 |
| Round of 64 | Adam OlsonNebraska Wesleyan def. Matthew VoissemSt. Norbert College | 6-1, 6-2 |
| Round of 64 | Morgan RossCarleton College def. Cam LongLuther College | 6-2, 6-2 |
| Round of 64 | Lucas LeDouxGrinnell College def. Zach KnudsenUW-Eau Claire | 7-6, 6-4, 10-3 |
| Round of 64 | Ben McKimmSaint John's University def. Corey DuncanCornell College | 6-2, 6-2 |
| Round of 64 | Jared SaueConcordia Moorhead def. Jared ScherlingNebraska Wesleyan | 6-1, 6-1 |
| Round of 64 | Jacob EndresGustavus Adolphus College def. Charlie ParishUW-La Crosse | 2-6, 6-3, 10-8 |
| Round of 64 | Johnny ReichmanCarleton College def. Henry MorrisBethel University | 7-5, 6-1 |
| Round of 64 | Aditya VasavanSt. Olaf def. Jeremy EllerbyWartburg | 3-6, 6-0, 10-7 |
| Round of 64 | Nick Van Den HandleCornell College def. Laine LarsonBethany Lutheran | 6-4, 6-1 |
| Round of 64 | Caleb UlringGrinnell College def. Jess HansenSaint John's University | 6-2, 6-3, retired |
| Round of 64 | CJ CliffCentral College def. Mitchel GjersethCarroll | 6-2, 6-1 |
| Round of 64 | Nick KnudsonBethel University def. Travis BeachMacalester | 6-2, 6-2 |
| Round of 64 | Landon RidpathNorthwestern (Minn.) def. Nathan KnappConcordia Wisconsin | 6-2, 6-2 |
| Round of 64 | Christian PurnellCarleton College def. Jesse SchneebergerConcordia Moorhead | 6-4, 6-4, 10-8 |
| Round of 64 | Zeke HaugenGustavus Adolphus College def. Ben KlimekHamline University | 6-1, 6-2 |
| Round of 64 | Joey ShubertUW-La Crosse def. Fumiya KitaharaWartburg | 6-4, 2-6, 11-9 |
| Round of 64 | Raghuram InturiGrinnell College def. Corey PenickHamline University | 6-0, 6-2 |
| Round of 64 | Zach JanssenUW-Eau Claire def. Alex ZuzekSaint Mary's University | 6-2, 6-1 |
| Round of 64 | Andrew SharngCarleton College def. Tommy WillarUW-La Crosse | 6-1, 6-3 |
| Round of 64 | Matthew EngumConcordia Moorhead def. Matheus BustamanteNebraska Wesleyan | 6-4, 1-6, 10-7 |
| Round of 64 | Christopher ProkoschSt. Olaf def. Lewis WhiteCarleton College | 6-3, 3-6, 10-7 |
| Round of 64 | Kenny GoinsLuther College def. Peter LindbergBethel University | 6-1, 6-1 |
| Round of 64 | Trevor BudewitzConcordia Wisconsin def. Joe OleniczakSt. Norbert College | 6-2, 6-2 |
| Round of 64 | L Dane SteidlUW-Eau Claire def. Zach StrawSt. Scholastica | 6-1, 6-1 |
| Round of 32 | Brandon KuetherHamline University def. Sam NettletonWartburg | 6-4, 6-3 |
| Round of 32 | Jonas Lindholm-UzziCarleton College def. Brady HicksSt. Norbert College | 6-2, 6-0 |
| Round of 32 | Riley PetersonUW-La Crosse def. Alex SenjemGustavus Adolphus College | 6-3, 3-6, 10-7 |
| Round of 32 | L Derek WilliamsNorthwestern (Minn.) def. Bryce GadkeSt. Scholastica | 7-5, 6-2 |
| Round of 32 | Morgan RossCarleton College def. Adam OlsonNebraska Wesleyan | 6-2, 6-3 |
| Round of 32 | Lucas LeDouxGrinnell College def. Ben McKimmSaint John's University | 6-3, 6-3 |
| Round of 32 | Jared SaueConcordia Moorhead def. Jacob EndresGustavus Adolphus College | 6-1, 6-2 |
| Round of 32 | Johnny ReichmanCarleton College def. Aditya VasavanSt. Olaf | 6-1, 6-0 |
| Round of 32 | Nick Van Den HandleCornell College def. Caleb UlringGrinnell College | 6-3, 6-0 |
| Round of 32 | Nick KnudsonBethel University def. CJ CliffCentral College | 6-0, 6-2 |
| Round of 32 | Christian PurnellCarleton College def. Landon RidpathNorthwestern (Minn.) | 7-6, 6-0 |
| Round of 32 | Joey ShubertUW-La Crosse def. Zeke HaugenGustavus Adolphus College | 3-6, 7-5, 10-5 |
| Round of 32 | Zach JanssenUW-Eau Claire def. Raghuram InturiGrinnell College | 6-2, 6-1 |
| Round of 32 | Andrew SharngCarleton College def. Matthew EngumConcordia Moorhead | 6-1, 6-1 |
| Round of 32 | Kenny GoinsLuther College def. Christopher ProkoschSt. Olaf | 6-2, 6-1 |
| Round of 32 | Dane SteidlUW-Eau Claire def. Trevor BudewitzConcordia Wisconsin | 6-0, 6-0 |
| Round of 16 | Jonas Lindholm-UzziCarleton College def. Brandon KuetherHamline University | 6-3, 6-1 |
| Round of 16 | Riley PetersonUW-La Crosse def. Derek WilliamsNorthwestern (Minn.) | 6-3, 6-1 |
| Round of 16 | Morgan RossCarleton College def. Lucas LeDouxGrinnell College | 6-2, 6-1 |
| Round of 16 | Johnny ReichmanCarleton College def. Jared SaueConcordia Moorhead | 6-3, 6-1 |
| Round of 16 | Nick Van Den HandleCornell College def. Nick KnudsonBethel University | 6-3, 6-4 |
| Round of 16 | Christian PurnellCarleton College def. Joey ShubertUW-La Crosse | 6-3, 3-6, 7-6 |
| Round of 16 | Andrew SharngCarleton College def. Zach JanssenUW-Eau Claire | 6-3, 6-7, 7-6 |
| Round of 16 | Dane SteidlUW-Eau Claire def. Kenny GoinsLuther College | 6-1, 6-2 |
| Quarterfinal | Riley PetersonUW-La Crosse def. Jonas Lindholm-UzziCarleton College | 7-5, 6-4, 7-6 |
| Quarterfinal | Johnny ReichmanCarleton College def. Morgan RossCarleton College | 6-2, 7-5 |
| Quarterfinal | Christian PurnellCarleton College def. Nick Van Den HandleCornell College | 6-4, 6-3 |
| Quarterfinal | Andrew SharngCarleton College def. Dane SteidlUW-Eau Claire | 6-4, 6-4 |
| Semifinal | Johnny ReichmanCarleton College def. Riley PetersonUW-La Crosse | 6-4, 6-1 |
| Semifinal | Andrew SharngCarleton College def. Christian PurnellCarleton College | 7-5, 7-5 |
| Final | Andrew SharngCarleton College def. Johnny ReichmanCarleton College | 6-2, 6-7, 10-5 |
