| Round of 128 | Tripp SchulteCarthage College def. Nathan RaskinConcordia Wisconsin | 6-0, 6-2 |
| Round of 128 | Suyash GuptaGustavus Adolphus def. Trisan FjelstadUniversity of St. Thomas | 6-3, 6-4 |
| Round of 128 | Shomas KishimotoCornell College def. Noah GuillermoWis.-Whitewater | 6-4, 3-6, 7-5 |
| Round of 128 | Daniel SchoenUW-Eau Claire def. Parker HearneWis.-Whitewater | 6-2, 6-1 |
| Round of 128 | Grant MortonLuther College def. Ben WhiteMacalester | 6-1, 6-5 |
| Round of 128 | Zach KantorBethel University def. Spencer WickSt. Olaf | 6-4, 6-5 |
| Round of 128 | Joseph HarrisonCarroll University def. Tou Ger XiongHamline University | 6-3, 6-2 |
| Round of 128 | Ishaan TibrewalGrinnell College def. Brandon DechterWis.-Whitewater | 6-0, 6-0 |
| Round of 128 | Nate JordreSaint John's University def. John NykyforukCarthage College | 6-2, 6-2 |
| Round of 128 | Anthony MooreUW La Crosse def. David YoungsConcordia-M'head | 6-4, 6-7, 6-3 |
| Round of 128 | Landon RidpathNorthwestern (Minn.) def. Jordan SchneckUniversity of St. Thomas | 4-6, 6-3, 6-4 |
| Round of 128 | Bobby TiedemanSaint Mary's University def. Peter KlodaConcordia Wisconsin | 6-4, 1-1, 6-2 |
| Round of 128 | Luke FordCoe College def. Matt KrzewinskiCarthage College | 5-7, 7-5, 6-2 |
| Round of 128 | Sahil ChhuganiCarleton College def. Renan BarrosUW-Eau Claire | 6-4, 6-5 |
| Round of 128 | Ben CobinGrinnell College vs. Erik BeckersBethel University | no result |
| Round of 128 | Ryan MitchellWis.-Whitewater def. Marius Dornhagen S.Edgewood College | 6-1, 6-4 |
| Round of 128 | Nate ParsonsLuther College def. Ryan MegerSaint John's University | 6-3, 6-4 |
| Round of 128 | Xavier SangaGustavus Adolphus def. Lucas HuffmanWartburg College | 6-5, 6-2 |
| Round of 128 | Cole HagmermanGrinnell College def. Tom GreeneCornell College | 6-1, 6-0 |
| Round of 128 | Nate AckertCoe College def. Adam BurkUW-Eau Claire | 6-2, 6-3 |
| Round of 128 | W Elliot SchneiderSt. Scholastica def. David BoschmaCentral | 6-2, 6-4 |
| Round of 128 | Nolan RademacherConcordia Wisconsin def. Sterling SiblingUniversity of St. Thomas | 6-3, 6-0 |
| Round of 128 | Elias RamirezHamline University def. Gus Fedje-JohnstonSt. Olaf | 6-0, 6-0 |
| Round of 128 | Xander RotiCarleton College def. Zach WoodWis.-Whitewater | 6-3, 6-4 |
| Round of 128 | Riley PetersonUW La Crosse def. Hayden DzurisinCornell College | 6-7, 6-1, 6-4 |
| Round of 128 | Daniel MooreCarthage College def. Karsten KnutsenMacalester | 6-4, 6-3 |
| Round of 128 | Robert RiderWis.-Whitewater def. Erich NussUniversity of St. Thomas | 5-7, 7-5, 6-4 |
| Round of 128 | Zach LaneGrinnell College def. Corey LokenSt. Olaf | 6-2, 6-4 |
| Round of 128 | Nate GreinerCoe College def. Joel HugGustavus Adolphus | 7-6, 6-2 |
| Round of 128 | Zach JanssenUW-Eau Claire def. Brett ConardWis.-Whitewater | 6-2, 6-2 |
| Round of 128 | William IsimingerCentral def. Gabe BinversieConcordia Wisconsin | 6-2, 7-6 |
| Round of 128 | Cole SchneiderLuther College def. Erik PorterConcordia-M'head | 6-0, 6-5 |
| Round of 128 | Samuel NettletonWartburg College def. Ian FosterCarroll University | 3-6, 6-4, 6-1 |
| Round of 128 | Thomas GillachSaint John's University def. Mouaad AlhouniGustavus Adolphus | 6-3, 6-0 |
| Round of 128 | Alex GrayWis.-Whitewater def. Eshan VarmaUniversity of St. Thomas | 6-1, 6-0 |
| Round of 128 | W Rafa GonzalezSt. Scholastica def. Sam StickelsGrinnell College | 6-1, 0-6, 7-6 |
| Round of 128 | Alex AltUW La Crosse def. Jeffrey JorgensenMacalester | 6-3, 7-6 |
| Round of 128 | W Serhii TykhonenkoSt. Scholastica def. Brendan PietilaWis.-Whitewater | 6-3, 6-1 |
| Round of 128 | Grant MautheUW-Eau Claire def. Brian MurmanLuther College | 6-4, 6-2 |
| Round of 128 | Xander ZuczekCarleton College def. Christian DoctorConcordia Wisconsin | 6-0, 6-0 |
| Round of 128 | M.Conlin-BrandenburgGrinnell College def. Fordy LeipoldCarthage College | 6-2, 6-2 |
| Round of 128 | Matthew PrimozicWis.-Whitewater def. Drew ArnoldCornell College | 6-1, 6-0 |
| Round of 128 | Joseph PunnooseGustavus Adolphus def. Brook NorwoodLuther College | 6-1, 6-4 |
| Round of 128 | Bowen MinceGrinnell College def. Andre AntreassianCarthage College | 6-3, 6-0 |
| Round of 128 | Chayce RoeckerCarroll University def. Nick VossenUniversity of St. Thomas | 6-3, 6-4 |
| Round of 128 | Charlie HarrisLoras College def. Sebastion SeegerEdgewood College | 6-2, 4-6, 6-1 |
| Round of 128 | Jimmy EngelhartWis.-Whitewater def. Hunter KrebsbachSaint John's University | 6-5, 6-0 |
| Round of 128 | Christopher ProkoschSt. Olaf def. Nazeer RobinsonHamline University | 6-3, 3-6, 6-4 |
| Round of 64 | Leo VithoontienCarleton College def. Tripp SchulteCarthage College | 6-0, 6-3 |
| Round of 64 | Suyash GuptaGustavus Adolphus def. Shomas KishimotoCornell College | 6-2, 3-6, 6-1 |
| Round of 64 | Rami HemaidanCoe College def. Daniel SchoenUW-Eau Claire | 6-2, 6-4 |
| Round of 64 | Grant MortonLuther College def. Zach KantorBethel University | 6-2, 6-1 |
| Round of 64 | Yassine DerbaniGustavus Adolphus def. Joseph HarrisonCarroll University | 6-2, 6-2 |
| Round of 64 | Nate JordreSaint John's University def. Ishaan TibrewalGrinnell College | 7-6, 6-3 |
| Round of 64 | Anthony MooreUW La Crosse def. Trevor HamiltonLoras College | 6-2, 4-6, 6-0 |
| Round of 64 | Landon RidpathNorthwestern (Minn.) def. Bobby TiedemanSaint Mary's University | 6-1, 5-7, 6-0 |
| Round of 64 | Chase JohnsonGustavus Adolphus def. Luke FordCoe College | 6-4, 6-2 |
| Round of 64 | Sahil ChhuganiCarleton College def. Ben CobinGrinnell College | 6-1, 6-0 |
| Round of 64 | Ryan MitchellWis.-Whitewater def. Kyle WogahnUW La Crosse | 6-2, 6-5 |
| Round of 64 | Nate ParsonsLuther College def. Xavier SangaGustavus Adolphus | 7-6, 6-0 |
| Round of 64 | Sam HochbergerMacalester def. Cole HagmermanGrinnell College | 6-3, 6-2 |
| Round of 64 | L Nate AckertCoe College def. Elliot SchneiderSt. Scholastica | 7-6, 6-1 |
| Round of 64 | Michael O'NeilGustavus Adolphus def. Nolan RademacherConcordia Wisconsin | 6-1, 6-0 |
| Round of 64 | Elias RamirezHamline University def. Xander RotiCarleton College | 6-7, 6-4, 6-3 |
| Round of 64 | Daniel MooreCarthage College def. Riley PetersonUW La Crosse | 6-5, 6-3 |
| Round of 64 | William WalshCarleton College def. Robert RiderWis.-Whitewater | 6-3, 6-1 |
| Round of 64 | Nate GreinerCoe College def. Zach LaneGrinnell College | 6-4, 6-2 |
| Round of 64 | Hunter FerneliusBethel University def. Zach JanssenUW-Eau Claire | 6-1, 6-3 |
| Round of 64 | Cole SchneiderLuther College def. William IsimingerCentral | 6-2, 6-0 |
| Round of 64 | Nick AneyGustavus Adolphus def. Samuel NettletonWartburg College | 6-1, 6-0 |
| Round of 64 | Alex GrayWis.-Whitewater def. Thomas GillachSaint John's University | 6-1, 6-4 |
| Round of 64 | L Jake TrondsonHamline University def. Rafa GonzalezSt. Scholastica | 6-2, 6-0 |
| Round of 64 | W Serhii TykhonenkoSt. Scholastica def. Alex AltUW La Crosse | 6-1, 0-6, 6-2 |
| Round of 64 | Indraneel RautGustavus Adolphus def. Grant MautheUW-Eau Claire | 6-3, 6-2 |
| Round of 64 | M.Conlin-BrandenburgGrinnell College def. Xander ZuczekCarleton College | 6-4, 6-2 |
| Round of 64 | Josh PudloCoe College def. Matthew PrimozicWis.-Whitewater | 6-5, 6-3 |
| Round of 64 | Joseph PunnooseGustavus Adolphus def. Bowen MinceGrinnell College | 6-4, 6-7, 6-2 |
| Round of 64 | Aaron GoodmanCarleton College def. Chayce RoeckerCarroll University | 6-4, 6-2 |
| Round of 64 | Jimmy EngelhartWis.-Whitewater def. Charlie HarrisLoras College | 6-0, 6-0 |
| Round of 64 | Patrick WhalingGustavus Adolphus def. Christopher ProkoschSt. Olaf | 6-1, 6-0 |
| Round of 32 | Leo VithoontienCarleton College def. Suyash GuptaGustavus Adolphus | 6-2, 6-1 |
| Round of 32 | Rami HemaidanCoe College def. Grant MortonLuther College | 6-2, 8-6 |
| Round of 32 | Yassine DerbaniGustavus Adolphus def. Nate JordreSaint John's University | 6-3, 6-1 |
| Round of 32 | Landon RidpathNorthwestern (Minn.) def. Anthony MooreUW La Crosse | 3-6, 7-5, 7-5 |
| Round of 32 | Chase JohnsonGustavus Adolphus def. Sahil ChhuganiCarleton College | 6-0, 6-2 |
| Round of 32 | Ryan MitchellWis.-Whitewater def. Nate ParsonsLuther College | 7-6, 6-0 |
| Round of 32 | Nate AckertCoe College def. Sam HochbergerMacalester | 6-2, 6-1 |
| Round of 32 | Michael O'NeilGustavus Adolphus def. Elias RamirezHamline University | 6-1, 6-3 |
| Round of 32 | William WalshCarleton College def. Anthony MooreUW La Crosse | 6-4, 6-0 |
| Round of 32 | Hunter FerneliusBethel University def. Nate GreinerCoe College | 6-3, 6-2 |
| Round of 32 | Nick AneyGustavus Adolphus def. Cole SchneiderLuther College | 3-6, 6-3, 7-6 |
| Round of 32 | Jake TrondsonHamline University def. Alex GrayWis.-Whitewater | 6-1, 6-3 |
| Round of 32 | L Indraneel RautGustavus Adolphus def. Serhii TykhonenkoSt. Scholastica | 6-1, 6-4 |
| Round of 32 | Josh PudloCoe College def. M.Conlin-BrandenburgGrinnell College | 6-3, 6-1 |
| Round of 32 | Joseph PunnooseGustavus Adolphus def. Aaron GoodmanCarleton College | 7-6, 6-4 |
| Round of 32 | Patrick WhalingGustavus Adolphus def. Jimmy EngelhartWis.-Whitewater | 6-0, 6-1 |
| Round of 16 | Leo VithoontienCarleton College def. Rami HemaidanCoe College | 6-1, 6-1 |
| Round of 16 | Yassine DerbaniGustavus Adolphus def. Landon RidpathNorthwestern (Minn.) | 6-2, 6-1 |
| Round of 16 | Chase JohnsonGustavus Adolphus def. Ryan MitchellWis.-Whitewater | 6-1, 6-0 |
| Round of 16 | Michael O'NeilGustavus Adolphus def. Nate AckertCoe College | 7-5, 7-5 |
| Round of 16 | William WalshCarleton College def. Hunter FerneliusBethel University | 7-5, 6-1 |
| Round of 16 | Jake TrondsonHamline University def. Nick AneyGustavus Adolphus | 6-1, 6-0 |
| Round of 16 | Indraneel RautGustavus Adolphus def. Josh PudloCoe College | 6-2, 6-4 |
| Round of 16 | Patrick WhalingGustavus Adolphus def. Joseph PunnooseGustavus Adolphus | 6-1, 6-1 |
| Quarterfinal | Leo VithoontienCarleton College def. Yassine DerbaniGustavus Adolphus | 6-3, 6-0 |
| Quarterfinal | Chase JohnsonGustavus Adolphus def. Michael O'NeilGustavus Adolphus | 6-2, 6-3 |
| Quarterfinal | Jake TrondsonHamline University def. William WalshCarleton College | 6-4, 6-2 |
| Quarterfinal | Patrick WhalingGustavus Adolphus def. Indraneel RautGustavus Adolphus | 6-1, 6-1 |
| Semifinal | Leo VithoontienCarleton College def. Chase JohnsonGustavus Adolphus | 6-2, 6-1 |
| Semifinal | Jake TrondsonHamline University def. Patrick WhalingGustavus Adolphus | 6-4, 6-2 |
| Final | Jake TrondsonHamline University def. Leo VithoontienCarleton College | 6-4, 7-6 |
