| Round of 128 | Mohanad AlhouniGustavus Adolphus College def. Jackson LewtonCentral College | 6-0, 6-0 |
| Round of 128 | Danny SchoenWisconsin-Eau Claire def. CJ LloydNorthwestern (Minn.) | 6-3, 6-0 |
| Round of 128 | Kevin MeiCarleton College def. Lucas MonterrosoWisconsin-Whitewater | 7-6, 7-6 |
| Round of 128 | Juan QuirogaDubuque def. Marius Dornhagen S.Edgewood College | 6-4, 6-4 |
| Round of 128 | Josh PudloCoe College def. Eshan VarmaSt. Thomas | 6-0, 6-0 |
| Round of 128 | Xavier SangaGustavus Adolphus College def. Adam OlsonNebraska Wesleyan | 6-2, 6-0 |
| Round of 128 | Peter JaegerCarroll University def. David SchneckConcordia Moorhead | 6-2, 6-4 |
| Round of 128 | Matt LindsayWisconsin-La Crosse def. Thomas GillachSaint John's University | 6-7, 6-4, 6-3 |
| Round of 128 | Josh DoyleMacalester def. Nolan RademacherConcordia University Wisconsin | 6-3, 7-5 |
| Round of 128 | Garret TaylorCentral College def. Ishaan TibrewalGrinnell College | 4-6, 6-0, 6-3 |
| Round of 128 | Michael O'NeilGustavus Adolphus College def. Jake KudrickCoe College | 2-6, 6-4, 6-1 |
| Round of 128 | Cole SchneiderLuther College def. Charlie HarrisLoras College | 6-3, 6-0 |
| Round of 128 | Yassine DerbaniGustavus Adolphus College def. Sahil ChhuganiCarleton College | 7-6, 6-1 |
| Round of 128 | Shoma KishimotoCornell College def. Cade FrancourLawrence University | 6-0, 6-0 |
| Round of 128 | Brandon DechterWisconsin-Whitewater def. Riley PetersonWisconsin-La Crosse | 6-1, 6-0 |
| Round of 128 | Jess HansenSaint John's University def. Brett GiesenSaint Mary's University | 5-7, 6-4, 6-3 |
| Round of 128 | Herman AbbanCarthage College def. Matt SerackiHamline University | 6-4, 6-1 |
| Round of 128 | W Elliot SchneiderSt. Scholastica def. Joe HarrisonCarroll University | 7-5, 6-2 |
| Round of 128 | Marty BeckSt. Thomas def. James ParadisinSt. Thomas | 6-0, 6-3 |
| Round of 128 | Andrew DahlWisconsin-Eau Claire def. Brett ConardWisconsin-Whitewater | 6-4, 6-1 |
| Round of 128 | Nate AckertCoe College def. David YoungsConcordia Moorhead | 6-2, 6-3 |
| Round of 128 | Matt ZurowskiWisconsin-Whitewater def. Alex ZuzekSaint Mary's University | 6-3, 6-0 |
| Round of 128 | Jordon O'KellyCarleton College def. Riley MichelLoras College | 6-0, 6-1 |
| Round of 128 | Jonah PunnooseSaint John's University def. Nathan RaskinConcordia University Wisconsin | 6-0, 6-3 |
| Round of 128 | Grant ThompsonWisconsin-Whitewater def. Sam HochbergerMacalester | 6-3, 6-0 |
| Round of 128 | Nate GreinerCoe College def. Kevin HurleyCarleton College | 7-6, 0-6, 6-4 |
| Round of 128 | Hunter FerneliusBethel University def. Ben CobinGrinnell College | 3-6, 6-4, 6-3 |
| Round of 128 | T. Connor ShivesGustavus Adolphus College def. Bobby TiedemanSaint Mary's University | 6-4, 6-2 |
| Round of 128 | Chase JohnsonGustavus Adolphus College def. Alex AltWisconsin-La Crosse | 6-0, 6-1 |
| Round of 128 | Nick VossenSt. Thomas def. Tucker BarnesCornell College | 7-5, 6-4 |
| Round of 128 | Grant MortonLuther College def. Connor MaloneyLawrence University | 6-1, 6-2 |
| Round of 128 | Sam NettletonWartburg College def. Tom PalmerCentral College | 6-2, 7-5 |
| Round of 128 | Erik PorterConcordia Moorhead def. Zach LeVeneSt. Thomas | 4-6, 7-5, 6-2 |
| Round of 128 | Gabe SteinwandGustavus Adolphus College def. Brian MurmanLuther College | 6-4, 6-4 |
| Round of 128 | Tom GreeneCornell College def. Gabe BinversieConcordia University Wisconsin | 6-4, 7-6 |
| Round of 128 | W Serhii TykhonenkoSt. Scholastica def. Matthew PrimozicWisconsin-Whitewater | 6-1, 6-2 |
| Round of 128 | M.Conlin-BrandenburgGrinnell College def. Jimmy CunninghamCentral College | 6-1, 6-4 |
| Round of 128 | Aaron GoodmanCarleton College def. Alex HolmSaint Mary's University | 6-2, 6-0 |
| Round of 128 | Renan BarrosWisconsin-Eau Claire def. Ben WhiteMacalester | 6-0, 6-1 |
| Round of 128 | Zane NavratilWisconsin-Whitewater def. Luke FordCoe College | 6-4, 6-1 |
| Round of 128 | Zach WoodWisconsin-Whitewater def. Nazeer RobinsonHamline University | 6-0, 6-2 |
| Round of 128 | Evgeny PakhomenkoCoe College def. Lawrence HiquianaGustavus Adolphus College | 7-6, 6-2 |
| Round of 128 | Andrew QiCarleton College def. Hale BreitNebraska Wesleyan | 6-1, 6-0 |
| Round of 128 | Tim LarsonSaint John's University def. Connor BarnardWartburg College | 6-2, 6-4 |
| Round of 128 | Chayce RoeckerCarroll University def. Bill Schuman-KlineLawrence University | 6-0, 6-4 |
| Round of 128 | Nate ParsonsLuther College def. Erich NussSt. Thomas | 6-2, 6-1 |
| Round of 128 | William IsimingerCentral College def. Kevin MurphyLoras College | 6-3, 6-0 |
| Round of 128 | Zach EksteinGustavus Adolphus College def. Matt RileyWisconsin-La Crosse | 6-4, 6-1 |
| Round of 128 | Sterling SibleySt. Thomas def. Robert RiderWisconsin-Whitewater | 6-3, 6-7, 6-3 |
| Round of 128 | Sriram SugumaranGrinnell College def. Mouaad AlhouniGustavus Adolphus College | 6-4, 6-0 |
| Round of 128 | Ryan MegerSaint John's University def. Sean BaldwinLoras College | 6-0, 6-0 |
| Round of 128 | Leo VithoontienCarleton College def. Anders JensenLuther College | 6-1, 6-2 |
| Round of 128 | Hayden DzurisinCornell College def. Sam GowanWisconsin-La Crosse | 6-4, 7-5 |
| Round of 128 | Zach JanssenWisconsin-Eau Claire def. Tyler NelsonCoe College | 6-2, 6-3 |
| Round of 128 | Aidan TirpackMacalester def. Jacob LoganCentral College | 6-0, 6-2 |
| Round of 128 | Patrick WhalingGustavus Adolphus College def. Matthew EngumConcordia Moorhead | 6-0, 6-0 |
| Round of 128 | Brad GuendelConcordia University Wisconsin def. Jacob KellerCentral College | 6-0, 6-0 |
| Round of 128 | Jimmy EngelhartWisconsin-Whitewater def. Brenden AmiotteSaint Mary's University | 6-4, 6-2 |
| Round of 128 | Zach KantorBethel University def. Gabe GuarinHamline University | 6-1, 6-3 |
| Round of 128 | Tommy EntwistleGustavus Adolphus College def. Aidan DelgadoLawrence University | 6-0, 6-0 |
| Round of 128 | Daniel MooreCarthage College def. Danny HoganSt. Olaf College | 6-2, 6-3 |
| Round of 128 | Kyle WogahnWisconsin-La Crosse def. Matthew YangMacalester | 6-4, 3-6, 7-6 |
| Round of 128 | Mason BultjeGustavus Adolphus College def. Xander ZuczekCarleton College | 7-6, 3-6, 6-4 |
| Round of 128 | Brady AndersonCoe College def. Augie BaduraWisconsin-Eau Claire | 6-0, 6-0 |
| Round of 64 | Mohanad AlhouniGustavus Adolphus College def. Danny SchoenWisconsin-Eau Claire | 6-0, 6-2 |
| Round of 64 | Kevin MeiCarleton College def. Juan QuirogaDubuque | 6-0, 6-0 |
| Round of 64 | Josh PudloCoe College def. Xavier SangaGustavus Adolphus College | 6-3, 7-5 |
| Round of 64 | Peter JaegerCarroll University def. Matt LindsayWisconsin-La Crosse | 6-3, 6-2 |
| Round of 64 | Josh DoyleMacalester def. Garret TaylorCentral College | 6-2, 6-4 |
| Round of 64 | Michael O'NeilGustavus Adolphus College def. Cole SchneiderLuther College | 5-7, 7-5, retired |
| Round of 64 | Yassine DerbaniGustavus Adolphus College def. Shoma KishimotoCornell College | 6-2, 6-2 |
| Round of 64 | Brandon DechterWisconsin-Whitewater def. Jess HansenSaint John's University | 6-0, 6-0 |
| Round of 64 | L Herman AbbanCarthage College def. Elliot SchneiderSt. Scholastica | 6-4, 6-0 |
| Round of 64 | Christian BeckSt. Olaf College def. Andrew DahlWisconsin-Eau Claire | 6-3, 5-7, 7-5 |
| Round of 64 | Nate AckertCoe College def. Matt ZurowskiWisconsin-Whitewater | 7-5, 6-3 |
| Round of 64 | Jordon O'KellyCarleton College def. Jonah PunnooseSaint John's University | 6-1, 6-0 |
| Round of 64 | Grant ThompsonWisconsin-Whitewater def. Nate GreinerCoe College | 6-2, 7-5 |
| Round of 64 | Hunter FerneliusBethel University def. T. Connor ShivesGustavus Adolphus College | 6-3, 4-6, 6-3 |
| Round of 64 | Chase JohnsonGustavus Adolphus College def. Nick VossenSt. Thomas | 6-1, 6-2 |
| Round of 64 | Grant MortonLuther College def. Sam NettletonWartburg College | 6-1, 6-2 |
| Round of 64 | Erik PorterConcordia Moorhead def. Gabe SteinwandGustavus Adolphus College | 6-4, 6-1 |
| Round of 64 | W Serhii TykhonenkoSt. Scholastica def. Tom GreeneCornell College | 6-0, 6-1 |
| Round of 64 | Aaron GoodmanCarleton College def. M.Conlin-BrandenburgGrinnell College | 6-0, 6-0 |
| Round of 64 | Zane NavratilWisconsin-Whitewater def. Renan BarrosWisconsin-Eau Claire | 6-2, 6-3 |
| Round of 64 | Zach WoodWisconsin-Whitewater vs. Evgeny PakhomenkoCoe College | 2-6, 6-4 |
| Round of 64 | Tim LarsonSaint John's University def. Andrew QiCarleton College | 6-4, 6-2 |
| Round of 64 | Nate ParsonsLuther College def. Chayce RoeckerCarroll University | 7-6, 6-3 |
| Round of 64 | Zach EksteinGustavus Adolphus College def. William IsimingerCentral College | 6-0, 6-1 |
| Round of 64 | Sriram SugumaranGrinnell College def. Sterling SibleySt. Thomas | 6-0, 6-1 |
| Round of 64 | Leo VithoontienCarleton College def. Ryan MegerSaint John's University | 6-1, 6-2 |
| Round of 64 | Zach JanssenWisconsin-Eau Claire def. Hayden DzurisinCornell College | 6-1, 6-2 |
| Round of 64 | Patrick WhalingGustavus Adolphus College def. Aidan TirpackMacalester | 6-2, 6-1 |
| Round of 64 | Jimmy EngelhartWisconsin-Whitewater def. Brad GuendelConcordia University Wisconsin | 6-2, 6-0 |
| Round of 64 | Tommy EntwistleGustavus Adolphus College def. Zach KantorBethel University | 6-4, 6-4 |
| Round of 64 | Kyle WogahnWisconsin-La Crosse def. Daniel MooreCarthage College | 6-4, 6-4 |
| Round of 64 | Brady AndersonCoe College def. Mason BultjeGustavus Adolphus College | 6-1, 6-1 |
| Round of 32 | Mohanad AlhouniGustavus Adolphus College def. Kevin MeiCarleton College | 6-1, 6-0 |
| Round of 32 | Josh PudloCoe College def. Peter JaegerCarroll University | 7-6, 6-2 |
| Round of 32 | Josh DoyleMacalester def. Michael O'NeilGustavus Adolphus College | 6-4, 1-6, 6-2 |
| Round of 32 | Yassine DerbaniGustavus Adolphus College def. Brandon DechterWisconsin-Whitewater | 6-1, 6-2 |
| Round of 32 | Herman AbbanCarthage College def. Christian BeckSt. Olaf College | 6-4, 6-3 |
| Round of 32 | Nate AckertCoe College def. Jordon O'KellyCarleton College | 6-3, 6-3 |
| Round of 32 | Hunter FerneliusBethel University def. Grant ThompsonWisconsin-Whitewater | 4-6, 6-2, 6-2 |
| Round of 32 | Chase JohnsonGustavus Adolphus College def. Grant MortonLuther College | 2-6, 6-2, 6-0 |
| Round of 32 | W Serhii TykhonenkoSt. Scholastica def. Erik PorterConcordia Moorhead | 6-3, 6-1 |
| Round of 32 | Zane NavratilWisconsin-Whitewater def. Aaron GoodmanCarleton College | 7-6, 6-1 |
| Round of 32 | Tim LarsonSaint John's University def. Evgeny PakhomenkoCoe College | 6-4, 5-7, 6-3 |
| Round of 32 | Zach EksteinGustavus Adolphus College def. Raghu InturiGrinnell College | 6-1, 6-1 |
| Round of 32 | Leo VithoontienCarleton College def. Sriram SugumaranGrinnell College | 7-6, 6-3 |
| Round of 32 | Patrick WhalingGustavus Adolphus College def. Zach JanssenWisconsin-Eau Claire | 6-2, 6-0 |
| Round of 32 | Tommy EntwistleGustavus Adolphus College def. Jimmy EngelhartWisconsin-Whitewater | 4-6, 7-5, 6-2 |
| Round of 32 | Brady AndersonCoe College def. Kyle WogahnWisconsin-La Crosse | 6-0, 6-3 |
| Round of 16 | Mohanad AlhouniGustavus Adolphus College def. Josh PudloCoe College | 6-3, 6-1 |
| Round of 16 | Yassine DerbaniGustavus Adolphus College def. Josh DoyleMacalester | 7-5, 6-1 |
| Round of 16 | Nate AckertCoe College def. Herman AbbanCarthage College | 7-6, 0-6, 7-5 |
| Round of 16 | Chase JohnsonGustavus Adolphus College def. Hunter FerneliusBethel University | 6-3, 6-2 |
| Round of 16 | W Serhii TykhonenkoSt. Scholastica def. Zane NavratilWisconsin-Whitewater | 5-7, 6-4, 6-4 |
| Round of 16 | Zach EksteinGustavus Adolphus College def. Tim LarsonSaint John's University | 6-1, 6-4 |
| Round of 16 | Patrick WhalingGustavus Adolphus College def. Leo VithoontienCarleton College | 7-6, 6-2 |
| Round of 16 | Brady AndersonCoe College def. Tommy EntwistleGustavus Adolphus College | 6-1, 6-2 |
| Quarterfinal | Mohanad AlhouniGustavus Adolphus College def. Yassine DerbaniGustavus Adolphus College | 6-1, 6-2 |
| Quarterfinal | Chase JohnsonGustavus Adolphus College def. Nate AckertCoe College | 6-2, 7-5 |
| Quarterfinal | L Zach EksteinGustavus Adolphus College def. Serhii TykhonenkoSt. Scholastica | 6-1, 6-4 |
| Quarterfinal | Brady AndersonCoe College def. Patrick WhalingGustavus Adolphus College | 5-7, 6-4, 7-6 |
| Semifinal | Mohanad AlhouniGustavus Adolphus College def. Chase JohnsonGustavus Adolphus College | 1-6, 6-1, 6-1 |
| Semifinal | Zach EksteinGustavus Adolphus College def. Brady AndersonCoe College | 6-4, 6-2 |
| Final | Mohanad AlhouniGustavus Adolphus College def. Zach EksteinGustavus Adolphus College | 6-2, 6-0 |
