| Round of 128 | Mohanad AlhouniGustavus Adolphus College def. Jacob LoganCentral College | 6-0, 6-0 |
| Round of 128 | Brenden AmiotteSaint Mary's University def. Gabriel SellmerNebraska Wesleyan | 6-1, 6-0 |
| Round of 128 | Kyle WogahnUW-La Crosse def. Anders JensenLuther College | 6-2, 6-4 |
| Round of 128 | Matt SerackiHamline University def. Bill Schuman-KlineLawrence University | 6-2, 1-6, retired |
| Round of 128 | Grant ThompsonUW-Whitewater def. Benjamin CobinGrinnell College | 6-2, 6-2 |
| Round of 128 | Patton McClellandCarleton College def. Erik PorterConcordia Moorhead | 6-0, 6-1 |
| Round of 128 | Michael MautheUW-Eau Claire def. Luke FordCoe College | 6-2, 6-4 |
| Round of 128 | W Logan EngelstadSt. Scholastica def. Tommy RundeSt. Thomas | 7-5, 5-7, 6-3 |
| Round of 128 | Luke ElifsonSt. Thomas def. Christian BeckSt. Olaf | 6-4, 6-3 |
| Round of 128 | Lukasz JaworskiCarthage College def. Ceejay SchaffnerConcordia Wisconsin | 7-5, 6-1 |
| Round of 128 | Kolin KiekhoeferBethel University def. Jaime BenavidesEdgewood College | 6-1, 6-1 |
| Round of 128 | Nate GreinerCoe College def. Sam StickelsGrinnell College | 7-6, 6-4 |
| Round of 128 | Chase JohnsonGustavus Adolphus College def. Peter JaegerCarroll | 6-3, 6-1 |
| Round of 128 | Aaron GoodmanCarleton College def. Tucker BarnesCornell College | 6-3, 6-1 |
| Round of 128 | Josh PudloCoe College def. Jonah PunnooseSaint John's University | 7-5, 6-1 |
| Round of 128 | Brian MurmanLuther College def. Vinnie GorskiUW-Eau Claire | 6-3, 6-4 |
| Round of 128 | Herman AbbanCarthage College def. Gabriel GuarinHamline University | 6-0, 6-1 |
| Round of 128 | L Lucas MonterrosoUW-Whitewater def. Makar GrytsevychSt. Scholastica | 6-0, 6-1 |
| Round of 128 | Mason BultjeGustavus Adolphus College def. Gabriel SouzaCornell College | 4-6, 6-4, 6-1 |
| Round of 128 | Jason DerbyLoras def. Will HamiltonGrinnell College | 6-4, 6-3 |
| Round of 128 | Zane NavratilUW-Whitewater def. Andrew DahlUW-Eau Claire | 6-0, 6-1 |
| Round of 128 | Evgeny PakhomenkoCoe College def. Joakim EdfeldtGustavus Adolphus College | 6-2, 6-2 |
| Round of 128 | Isaac ToivonenConcordia Moorhead def. Tommy SchubertSt. Thomas | 6-2, 6-2 |
| Round of 128 | Hardt BergmannMacalester def. Ryan MegerSaint John's University | 6-3, 6-4 |
| Round of 128 | Jose ColomaGrinnell College def. Evan StoneEdgewood College | 6-0, 6-0 |
| Round of 128 | Augie BaduraUW-Eau Claire def. Joseph HarrisonCarroll | 5-7, 6-4, 6-4 |
| Round of 128 | T. Connor ShivesGustavus Adolphus College def. Alex VandenbergSt. Norbert College | 6-1, 6-2 |
| Round of 128 | Matt PrimozicUW-Whitewater def. Joey SchneiderUW-La Crosse | 2-6, 7-6, 6-2 |
| Round of 128 | Brandon DechterUW-Whitewater def. Nate AckertCoe College | 7-5, 6-2, 6-4 |
| Round of 128 | Sahil ChhuganiCarleton College def. Burke AndersonSt. Thomas | 7-5, 6-2 |
| Round of 128 | Trent SchneiderLuther College def. Hunter FerneliusBethel University | 2-6, 6-2, 6-4 |
| Round of 128 | Brandon HornbackWartburg def. Christian DocterConcordia Wisconsin | 7-5, 2-6, 6-4 |
| Round of 128 | David JumesLawrence University def. Ben Vande ZandeSt. Norbert College | 7-6, 6-4 |
| Round of 128 | James McManusCoe College def. Zachary WoodUW-Whitewater | 7-6, 6-2 |
| Round of 128 | Tommy PitcherGrinnell College def. Danny HoganSt. Olaf | 6-0, 6-1 |
| Round of 128 | Tim LarsonSaint John's University def. Sam DykstraCentral College | 6-0, 6-1 |
| Round of 128 | Will WeyenburgUW-Eau Claire def. Marty BeckSt. Thomas | 6-1, 6-3 |
| Round of 128 | Pawel JaworskiCarthage College def. Sam BuffingtonLuther College | 6-0, 6-5 |
| Round of 128 | Ezra FrankelCarleton College def. Aditya GoyalCornell College | 6-3, 6-3 |
| Round of 128 | Gabe SteinwandGustavus Adolphus College def. Josh DoyleMacalester | 6-2, 7-5 |
| Round of 128 | James ForsterConcordia Wisconsin def. Brian DavenportEdgewood College | 6-0, 6-1 |
| Round of 128 | Jimmy EnglehartUW-Whitewater def. Ben WaitSt. Thomas | 6-3, 7-5 |
| Round of 128 | Chayce RoeckerCarroll def. David SchneckConcordia Moorhead | 7-6, 7-5 |
| Round of 128 | Matt SchullBethel University def. Mark ConradCarleton College | 6-2, 6-2 |
| Round of 128 | Cody JahrigHamline University def. Matt RileyUW-La Crosse | 6-4, 6-3 |
| Round of 128 | Alex BerntCoe College def. Henry JohnsonGrinnell College | 6-0, 6-1 |
| Round of 128 | Nate ParsonLuther College def. Conrad FeltenUW-Eau Claire | 6-2, 6-4 |
| Round of 128 | W Serhii TykhonenkoSt. Scholastica def. Zach EksteinGustavus Adolphus College | 6-2, 5-7, 6-2 |
| Round of 128 | Connor BarnardWartburg def. CJ LloydNorthwestern (Minn.) | 7-5, 6-2 |
| Round of 128 | Jake SmithLuther College def. Jordan O'KellyCarleton College | 6-2, 6-0 |
| Round of 128 | Andrew RustUW-Eau Claire def. Sterling SibleySt. Thomas | 6-3, 6-1 |
| Round of 128 | Patrick WhalingGustavus Adolphus College def. Kevin MurphyLoras | 6-0, 6-0 |
| Round of 128 | Garret TaylorCentral College def. Peter WillenborgMacalester | 6-4, 6-4 |
| Round of 128 | Cole MillerGrinnell College def. Hunter KrebsbachSaint John's University | 6-2, 6-3 |
| Round of 128 | Michael O'NeilGustavus Adolphus College def. David YoungsConcordia Moorhead | 6-1, 6-1 |
| Round of 128 | Rithwik RamanUW-Whitewater def. Chad MoklestadCoe College | 6-2, 6-3 |
| Round of 128 | W Ernesto TellesSt. Scholastica def. Brett GiesenSaint Mary's University | 6-1, 6-0 |
| Round of 128 | Yassine DerbaniGustavus Adolphus College def. Hayden DzurisinCornell College | 6-1, 6-2 |
| Round of 128 | Rory CalabriaUW-Whitewater def. Zach LaneGrinnell College | 6-4, 6-3 |
| Round of 128 | Kyle AppelLuther College def. Danny SchoenUW-Eau Claire | 6-2, 6-3 |
| Round of 128 | Pedro BethlemNebraska Wesleyan def. Brad GuendelConcordia Wisconsin | 6-7, 7-6, 6-0 |
| Round of 128 | Chris ConleyCarthage College def. Sam HohenshellSt. Olaf | 7-6, 6-0 |
| Round of 128 | Scott WallSt. Thomas def. Austin StefanichUW-La Crosse | 6-3, 3-6, 7-6 |
| Round of 128 | Brady AndersonCoe College def. Brett ConradUW-Whitewater | 6-0, 6-0 |
| Round of 64 | Mohanad AlhouniGustavus Adolphus College def. Brenden AmiotteSaint Mary's University | 6-1, 6-2 |
| Round of 64 | Kyle WogahnUW-La Crosse def. Matt SerackiHamline University | 6-3, 4-6, 6-4 |
| Round of 64 | Patton McClellandCarleton College def. Grant ThompsonUW-Whitewater | 6-1, 6-3 |
| Round of 64 | W Logan EngelstadSt. Scholastica def. Michael MautheUW-Eau Claire | 7-6, 6-0, 5-4, retired |
| Round of 64 | Luke ElifsonSt. Thomas def. Lukasz JaworskiCarthage College | 6-2, 6-0 |
| Round of 64 | Kolin KiekhoeferBethel University def. Nate GreinerCoe College | 6-3, 6-4 |
| Round of 64 | Chase JohnsonGustavus Adolphus College def. Aaron GoodmanCarleton College | 6-3, 6-2 |
| Round of 64 | Josh PudloCoe College def. Brian MurmanLuther College | 6-0, 6-0 |
| Round of 64 | Herman AbbanCarthage College def. Lucas MonterrosoUW-Whitewater | 6-3, 6-4 |
| Round of 64 | Mason BultjeGustavus Adolphus College def. Jason DerbyLoras | 6-4, 6-4 |
| Round of 64 | Zane NavratilUW-Whitewater def. Evgeny PakhomenkoCoe College | 7-6, 7-5 |
| Round of 64 | Isaac ToivonenConcordia Moorhead def. Hardt BergmannMacalester | 6-0, 6-1 |
| Round of 64 | Jose ColomaGrinnell College def. Augie BaduraUW-Eau Claire | 6-3, 6-4 |
| Round of 64 | T. Connor ShivesGustavus Adolphus College def. Matt PrimozicUW-Whitewater | 6-1, 6-4 |
| Round of 64 | Brandon DechterUW-Whitewater def. Sahil ChhuganiCarleton College | 6-3, 6-2 |
| Round of 64 | Trent SchneiderLuther College def. Brandon HornbackWartburg | 6-1, 6-0 |
| Round of 64 | James McManusCoe College def. David JumesLawrence University | 6-3, 3-6, 6-1 |
| Round of 64 | Tommy PitcherGrinnell College def. Tim LarsonSaint John's University | 7-5, 6-4 |
| Round of 64 | Will WeyenburgUW-Eau Claire def. Pawel JaworskiCarthage College | 6-4, 3-6, 6-3 |
| Round of 64 | Gabe SteinwandGustavus Adolphus College def. Ezra FrankelCarleton College | 6-1, 6-2 |
| Round of 64 | Jimmy EnglehartUW-Whitewater def. James ForsterConcordia Wisconsin | 6-0, 6-3 |
| Round of 64 | Matt SchullBethel University def. Chayce RoeckerCarroll | 6-2, 6-3 |
| Round of 64 | Alex BerntCoe College def. Matt RileyUW-La Crosse | 6-1, 6-4 |
| Round of 64 | L Nate ParsonLuther College def. Serhii TykhonenkoSt. Scholastica | 6-4, 2-6, 6-4 |
| Round of 64 | Jordan O'KellyCarleton College def. Connor BarnardWartburg | 6-2, 6-1 |
| Round of 64 | Patrick WhalingGustavus Adolphus College def. Andrew RustUW-Eau Claire | 6-0, 6-2 |
| Round of 64 | Cole MillerGrinnell College def. Garret TaylorCentral College | 6-4, 6-3 |
| Round of 64 | Rithwik RamanUW-Whitewater def. Michael O'NeilGustavus Adolphus College | 6-2, 6-3 |
| Round of 64 | L Yassine DerbaniGustavus Adolphus College def. Ernesto TellesSt. Scholastica | 7-6, 6-1, retired |
| Round of 64 | Kyle AppelLuther College def. Rory CalabriaUW-Whitewater | 6-2, 6-3 |
| Round of 64 | Chris ConleyCarthage College def. Pedro BethlemNebraska Wesleyan | 6-2, 6-2 |
| Round of 64 | Scott WallSt. Thomas def. Brady AndersonCoe College | 6-1, 6-1 |
| Round of 32 | Mohanad AlhouniGustavus Adolphus College def. Kyle WogahnUW-La Crosse | 6-0, 6-0 |
| Round of 32 | L Grant ThompsonUW-Whitewater def. Logan EngelstadSt. Scholastica | 6-3, 6-1 |
| Round of 32 | Luke ElifsonSt. Thomas def. Kolin KiekhoeferBethel University | 6-2, 6-1 |
| Round of 32 | Chase JohnsonGustavus Adolphus College def. Josh PudloCoe College | 3-6, 7-6, 6-1 |
| Round of 32 | Herman AbbanCarthage College def. Mason BultjeGustavus Adolphus College | 6-0, 6-1 |
| Round of 32 | Evgeny PakhomenkoCoe College def. Isaac ToivonenConcordia Moorhead | 3-6, 6-3, 6-2 |
| Round of 32 | Jose ColomaGrinnell College def. T. Connor ShivesGustavus Adolphus College | 1-6, 6-3, 6-3 |
| Round of 32 | Brandon DechterUW-Whitewater def. Trent SchneiderLuther College | 6-2, 5-7, 6-2 |
| Round of 32 | James McManusCoe College def. Tommy PitcherGrinnell College | 6-0, 6-1 |
| Round of 32 | Gabe SteinwandGustavus Adolphus College def. Will WeyenburgUW-Eau Claire | 6-2, 6-3 |
| Round of 32 | Jimmy EnglehartUW-Whitewater def. Matt SchullBethel University | 6-1, 1-6, 6-0 |
| Round of 32 | Alex BerntCoe College def. Nate ParsonLuther College | 7-5, 6-2 |
| Round of 32 | Patrick WhalingGustavus Adolphus College def. Jordan O'KellyCarleton College | 6-2, 6-2 |
| Round of 32 | Rithwik RamanUW-Whitewater def. Cole MillerGrinnell College | 6-1, 6-3 |
| Round of 32 | Kyle AppelLuther College def. Yassine DerbaniGustavus Adolphus College | 6-2, 6-1 |
| Round of 32 | Brady AndersonCoe College def. Chris ConleyCarthage College | 6-3, 6-0 |
| Round of 16 | Mohanad AlhouniGustavus Adolphus College def. Grant ThompsonUW-Whitewater | 6-2, 6-3 |
| Round of 16 | Chase JohnsonGustavus Adolphus College def. Luke ElifsonSt. Thomas | 6-2, 6-0, 7-5 |
| Round of 16 | Herman AbbanCarthage College def. Isaac ToivonenConcordia Moorhead | 6-1, 6-2 |
| Round of 16 | Jose ColomaGrinnell College def. Brandon DechterUW-Whitewater | 7-6, 1-6, 6-1 |
| Round of 16 | James McManusCoe College def. Gabe SteinwandGustavus Adolphus College | 6-3, 6-1 |
| Round of 16 | Alex BerntCoe College def. Jimmy EnglehartUW-Whitewater | 6-2, 7-5 |
| Round of 16 | Patrick WhalingGustavus Adolphus College def. Rithwik RamanUW-Whitewater | 3-6, 6-2, 6-1 |
| Round of 16 | Brady AndersonCoe College def. Kyle AppelLuther College | 6-1, 6-2 |
| Quarterfinal | Mohanad AlhouniGustavus Adolphus College def. Chase JohnsonGustavus Adolphus College | 6-1, 6-2 |
| Quarterfinal | Herman AbbanCarthage College def. Jose ColomaGrinnell College | 6-1, 6-1 |
| Quarterfinal | Alex BerntCoe College def. James McManusCoe College | 6-2, 1-6, 7-5 |
| Quarterfinal | Patrick WhalingGustavus Adolphus College def. Brady AndersonCoe College | 3-6, 6-3, 6-1 |
| Semifinal | Mohanad AlhouniGustavus Adolphus College def. Herman AbbanCarthage College | 6-7, 7-5, 6-1 |
| Semifinal | Patrick WhalingGustavus Adolphus College def. Alex BerntCoe College | 6-1, 6-2 |
| Final | Mohanad AlhouniGustavus Adolphus College def. Patrick WhalingGustavus Adolphus College | 6-2, 6-2 |
