| Round of 128 | Jake HumphreysWis.-Whitewater def. Jordan VerbauwhedeCarthage University | 6-4, 6-0 |
| Round of 128 | Christian NagyCarleton College def. Matt LindsayUW-La Crosse | 7-6, 7-6 |
| Round of 128 | Jack HansenSaint John's University def. Nate AckertCoe College | 5-7, 6-2, 10-7 |
| Round of 128 | Gabe SteinwandGustavus Adolphus College def. Tracy JohnsonGrinnell College | 6-4, 4-6, 10-6 |
| Round of 128 | Kyle AppelLuther College def. David YanagitaHamline University | 6-1, 6-2 |
| Round of 128 | Kyle HoffamnU W Eau Claire def. Ben CarlsonSt. Olaf | 6-2, 6-2 |
| Round of 128 | Matt SchullBethel University def. Colin SandgrenGustavus Adolphus College | 6-2, 6-1 |
| Round of 128 | Rory CalabriaWis.-Whitewater def. Allen-Michael MuenchUniversity of Saint Thomas | 6-3, 6-1 |
| Round of 128 | Andres SaenzGustavus Adolphus College def. Sam SticklesGrinnell College | 6-1, 6-0 |
| Round of 128 | W Josh StainerSt. Scholastica def. Brent HeflinBethany Lutheran College | 6-1, 6-0 |
| Round of 128 | Brian UtzMacalester def. Miguel PerezWis.-Whitewater | 6-1, 2-6, 10-8 |
| Round of 128 | Gabriel SouzaCornell College def. Brandon HornbackWartburg College | 6-6, 6-2 |
| Round of 128 | Zane NavratilWis.-Whitewater def. Josh PudloCoe College | 6-4, 6-4 |
| Round of 128 | Kevin HurleyCarleton College def. Andrew DahlU W Eau Claire | 7-6, 6-7, 10-8 |
| Round of 128 | Luke ElifsonUniversity of Saint Thomas def. Benjamin NommensenConcordia Wisconsin | 6-4, 6-1 |
| Round of 128 | Patrick WhalingGustavus Adolphus College def. Garret TaylorCentral College | 6-1, 6-2 |
| Round of 128 | Brady AndersonCoe College def. Alex FerruzziCarthage University | 6-1, 6-0 |
| Round of 128 | Nate ParsonsLuther College def. Burke AndersonUniversity of Saint Thomas | 6-7, 6-2, 10-7 |
| Round of 128 | Mitch ElofsonGustavus Adolphus College def. Joey SchneiderUW-La Crosse | 6-1, 6-3 |
| Round of 128 | CJ RayGrinnell College def. Andrew NagelSaint John's University | 6-5, 6-2 |
| Round of 128 | L Isaac ToivonenConcordia Minnesota def. Logan EngelstadSt. Scholastica | 4-6, 6-0, 10-8 |
| Round of 128 | Mike SchroederSt. Olaf def. Matt SerackiHamline University | 6-4, 6-3 |
| Round of 128 | Peter JaegerCarroll University def. Jordon StevensU W Eau Claire | 6-2, 4-6, 10-4 |
| Round of 128 | Aidan TirpackMacalester def. Ben KleinWis.-Whitewater | 3-6, 6-4, 13-11 |
| Round of 128 | Kevin MeiCarleton College def. Tony MirasolaUW-La Crosse | 6-3, 6-1 |
| Round of 128 | Ben WaitUniversity of Saint Thomas def. Matt ZurowskiWis.-Whitewater | 5-7, 6-3, 10-7 |
| Round of 128 | T. Connor ShivesGustavus Adolphus College def. Sam CatanzaroGrinnell College | 6-5, 6-3 |
| Round of 128 | Mike MautheU W Eau Claire def. Tyrin WagesCoe College | 6-0, 6-2 |
| Round of 128 | Grant ThompsonWis.-Whitewater def. Collin KaczorowskiSaint Mary's University | 6-2, 6-0 |
| Round of 128 | Sam BuffingtonLuther College def. Tucker BarnesCornell College | 6-3, 6-1 |
| Round of 128 | Pawel JaworskiCarthage University def. Brian DeCorteLawrence University | 6-4, 6-3 |
| Round of 128 | David HagbergGustavus Adolphus College def. Brett JacobusNorthwestern (Minn.) | 6-0, 3-3 |
| Round of 128 | Aaron GoodmanCarleton College def. Austin StefanichUW-La Crosse | 6-0, 6-2 |
| Round of 128 | Ryan JumpCarthage University def. Will WeyenbergU W Eau Claire | 6-1, 6-1 |
| Round of 128 | Brandon DechterWis.-Whitewater def. Zack DeckerCoe College | 6-7, 6-2, 10-5 |
| Round of 128 | Zack EksteinGustavus Adolphus College def. Tom SchubertUniversity of Saint Thomas | 6-0, 6-0 |
| Round of 128 | Scott WallUniversity of Saint Thomas def. Gabriel GuarinHamline University | 6-4, 6-3 |
| Round of 128 | Matt BisbeeWis.-Whitewater def. Mason BultjeGustavus Adolphus College | 5-7, 6-1, 10-6 |
| Round of 128 | Zach ZiturConcordia Minnesota def. Tom PalmerCentral College | 6-0, 6-1 |
| Round of 128 | Jose ColomaGrinnell College def. Christian DocterConcordia Wisconsin | 6-2, 6-0 |
| Round of 128 | Chase JohnsonGustavus Adolphus College def. Andrew GolotaWis.-Whitewater | 6-1, 6-0 |
| Round of 128 | Alex BerntCoe College def. Ben LahrenSaint John's University | 6-3, 6-3 |
| Round of 128 | Kolin KiekhoferBethel University def. David JumesLawrence University | 6-2, 0-6, 10-7 |
| Round of 128 | Joshua DoyleMacalester def. Christian BeckSt. Olaf | 6-4, 6-1 |
| Round of 128 | Matthew MonaghanGustavus Adolphus College def. Caleb KumarGrinnell College | 6-0, 6-2 |
| Round of 128 | Trent SchneiderLuther College def. Quentin LammersCarroll University | 6-1, 6-3 |
| Round of 128 | Matt KavanaghUniversity of Saint Thomas def. Evan StoneEdgewood College | 6-1, 6-4 |
| Round of 128 | L Michael TreisWis.-Whitewater def. Makar GrytsevychSt. Scholastica | 6-0, 6-3 |
| Round of 128 | Michael SchnarrWis.-Whitewater def. Anders JensenLuther College | 6-1, 6-2 |
| Round of 128 | Andrew RustU W Eau Claire def. Brady RadermacherUniversity of Saint Thomas | 6-7, 6-4, 10-1 |
| Round of 128 | Cole MillerGrinnell College def. Jordon O'KellyCarleton College | 6-3, 6-7, 10-7 |
| Round of 128 | Chris ConleyCarthage University def. Kyle McGraneUW-La Crosse | 7-6, 2-2, 1-0 |
| Round of 128 | Tim LarsonSaint John's University def. Ben Vande ZandeSt. Norbert College | 6-1, 6-2 |
| Round of 128 | Tommy EntwistleGustavus Adolphus College def. Evengy PakhomenkoCoe College | 6-4, 6-2 |
| Round of 128 | Connor BarnardWartburg College def. CJ LloydNorthwestern (Minn.) | 6-2, 6-2 |
| Round of 128 | R. Rajshekhar RamanWis.-Whitewater def. West AdelmanCentral College | 6-2, 6-5 |
| Round of 128 | Bryson CaleGrinnell College def. Brad GuendelConcordia Wisconsin | 6-1, 6-2 |
| Round of 128 | Alex BoomgardenCarthage University def. Thomas WeissCornell College | 6-1, 1-0 |
| Round of 128 | Conrad FeltenU W Eau Claire def. Cody JahrigHamline University | 6-3, 6-2 |
| Round of 128 | Joey KronzerSt. Olaf def. Patton McClellandCarleton College | 6-4, 6-2 |
| Round of 128 | Jimmy EngelhartWis.-Whitewater def. Kyle WogahnUW-La Crosse | 6-1, 2-6, 10-8 |
| Round of 128 | Mohanad Al HouniGustavus Adolphus College def. Tommy RundeUniversity of Saint Thomas | 6-0, 6-0 |
| Round of 128 | L Chad MoklestadCoe College def. Mike FontanaSt. Scholastica | 6-1, 6-0 |
| Round of 128 | Max GordonWis.-Whitewater def. Taylor ParrGustavus Adolphus College | 6-2, 1-6, 10-7 |
| Round of 64 | Jake HumphreysWis.-Whitewater def. Christian NagyCarleton College | 6-1, 6-2 |
| Round of 64 | Gabe SteinwandGustavus Adolphus College def. Jack HansenSaint John's University | 6-1, 6-5 |
| Round of 64 | Kyle AppelLuther College def. Kyle HoffamnU W Eau Claire | 6-4, 6-2 |
| Round of 64 | Rory CalabriaWis.-Whitewater def. Matt SchullBethel University | 6-5, 6-4 |
| Round of 64 | L Andres SaenzGustavus Adolphus College def. Josh StainerSt. Scholastica | 6-3, 6-3 |
| Round of 64 | Brian UtzMacalester def. Gabriel SouzaCornell College | 6-1, 6-6 |
| Round of 64 | Zane NavratilWis.-Whitewater def. Kevin HurleyCarleton College | 1-6, 6-2, 11-9 |
| Round of 64 | Luke ElifsonUniversity of Saint Thomas def. Patrick WhalingGustavus Adolphus College | 6-1, 6-4 |
| Round of 64 | Burke AndersonUniversity of Saint Thomas def. Nate ParsonsLuther College | 6-2, 6-0 |
| Round of 64 | Mitch ElofsonGustavus Adolphus College def. CJ RayGrinnell College | 6-2, 6-1 |
| Round of 64 | Isaac ToivonenConcordia Minnesota def. Mike SchroederSt. Olaf | 6-2, 6-1 |
| Round of 64 | Aidan TirpackMacalester def. Peter JaegerCarroll University | 6-2, 6-6 |
| Round of 64 | Kevin MeiCarleton College def. Ben WaitUniversity of Saint Thomas | 6-2, 6-3 |
| Round of 64 | T. Connor ShivesGustavus Adolphus College def. Mike MautheU W Eau Claire | 4-6, 6-4, 10-8 |
| Round of 64 | Grant ThompsonWis.-Whitewater def. Sam BuffingtonLuther College | 6-1, 6-0 |
| Round of 64 | David HagbergGustavus Adolphus College def. Pawel JaworskiCarthage University | 6-2, 4-6, 10-4 |
| Round of 64 | Ryan JumpCarthage University def. Aaron GoodmanCarleton College | 6-0, 6-2 |
| Round of 64 | Zack EksteinGustavus Adolphus College def. Brandon DechterWis.-Whitewater | 6-1, 6-4 |
| Round of 64 | Matt BisbeeWis.-Whitewater def. Scott WallUniversity of Saint Thomas | 6-5, 6-0 |
| Round of 64 | Jose ColomaGrinnell College def. Zach ZiturConcordia Minnesota | 6-0, 6-3 |
| Round of 64 | Alex BerntCoe College def. Chase JohnsonGustavus Adolphus College | 6-2, 6-5 |
| Round of 64 | Joshua DoyleMacalester def. Kolin KiekhoferBethel University | 6-1, 2-6, 10-7 |
| Round of 64 | Trent SchneiderLuther College def. Matthew MonaghanGustavus Adolphus College | 4-6, 6-1, 11-9 |
| Round of 64 | Michael TreisWis.-Whitewater def. Matt KavanaghUniversity of Saint Thomas | 6-1, 6-2 |
| Round of 64 | Michael SchnarrWis.-Whitewater def. Andrew RustU W Eau Claire | 6-4, 6-4 |
| Round of 64 | Cole MillerGrinnell College def. Chris ConleyCarthage University | 6-5, 6-3 |
| Round of 64 | Tommy EntwistleGustavus Adolphus College def. Tim LarsonSaint John's University | 6-4, 6-6 |
| Round of 64 | R. Rajshekhar RamanWis.-Whitewater def. Connor BarnardWartburg College | 6-1, 6-1 |
| Round of 64 | Max GordonWis.-Whitewater def. Chad MoklestadCoe College | 6-0, 6-3 |
| Round of 64 | Alex BoomgardenCarthage University def. Bryson CaleGrinnell College | 6-0, 6-2 |
| Round of 64 | Conrad FeltenU W Eau Claire def. Joey KronzerSt. Olaf | 6-4, 0-6, 10-1 |
| Round of 64 | Mohanad Al HouniGustavus Adolphus College def. Jimmy EngelhartWis.-Whitewater | 6-2, 6-1 |
| Round of 32 | Jake HumphreysWis.-Whitewater def. Gabe SteinwandGustavus Adolphus College | 6-1, 6-2 |
| Round of 32 | Kyle AppelLuther College def. Rory CalabriaWis.-Whitewater | 6-2, 6-1 |
| Round of 32 | Andres SaenzGustavus Adolphus College def. Brian UtzMacalester | 6-2, 6-0 |
| Round of 32 | Zane NavratilWis.-Whitewater def. Luke ElifsonUniversity of Saint Thomas | 6-2, 6-2 |
| Round of 32 | Brady AndersonCoe College def. Mitch ElofsonGustavus Adolphus College | 6-2, 6-3 |
| Round of 32 | Isaac ToivonenConcordia Minnesota def. Aidan TirpackMacalester | 4-6, 6-4, 10-6 |
| Round of 32 | T. Connor ShivesGustavus Adolphus College def. Kevin MeiCarleton College | 6-3, 6-2 |
| Round of 32 | Grant ThompsonWis.-Whitewater def. David HagbergGustavus Adolphus College | 6-1, 6-1 |
| Round of 32 | Zack EksteinGustavus Adolphus College def. Ryan JumpCarthage University | 6-3, 6-4 |
| Round of 32 | Jose ColomaGrinnell College def. Matt BisbeeWis.-Whitewater | 6-1, 6-2 |
| Round of 32 | Alex BerntCoe College def. Joshua DoyleMacalester | 6-3, 6-4 |
| Round of 32 | Michael TreisWis.-Whitewater def. Trent SchneiderLuther College | 6-1, 6-0 |
| Round of 32 | Cole MillerGrinnell College def. Michael SchnarrWis.-Whitewater | 3-6, 6-2, 10-4 |
| Round of 32 | R. Rajshekhar RamanWis.-Whitewater def. Tommy EntwistleGustavus Adolphus College | 6-7, 6-4, 15-13 |
| Round of 32 | Max GordonWis.-Whitewater def. Alex BoomgardenCarthage University | 6-3, 6-5 |
| Round of 32 | Mohanad Al HouniGustavus Adolphus College def. Conrad FeltenU W Eau Claire | 6-1, 6-0 |
| Round of 16 | Jake HumphreysWis.-Whitewater def. Kyle AppelLuther College | 6-1, 6-2 |
| Round of 16 | Andres SaenzGustavus Adolphus College def. Zane NavratilWis.-Whitewater | 6-3, 6-1 |
| Round of 16 | Brady AndersonCoe College def. Isaac ToivonenConcordia Minnesota | 6-0, 6-1 |
| Round of 16 | Grant ThompsonWis.-Whitewater def. T. Connor ShivesGustavus Adolphus College | 6-1, 6-4 |
| Round of 16 | Zack EksteinGustavus Adolphus College def. Jose ColomaGrinnell College | 6-4, 6-1 |
| Round of 16 | Alex BerntCoe College def. Michael TreisWis.-Whitewater | 2-6, retired |
| Round of 16 | R. Rajshekhar RamanWis.-Whitewater def. Cole MillerGrinnell College | 6-2, 6-0 |
| Round of 16 | Mohanad Al HouniGustavus Adolphus College def. Alex BoomgardenCarthage University | 6-1, 6-3 |
| Quarterfinal | Brady AndersonCoe College def. Grant ThompsonWis.-Whitewater | 6-2, 0-6, 7-6 |
| Quarterfinal | Zack EksteinGustavus Adolphus College def. Alex BerntCoe College | 6-4, 3-6, 6-1 |
| Quarterfinal | Mohanad Al HouniGustavus Adolphus College def. R. Rajshekhar RamanWis.-Whitewater | 6-3, 6-3 |
| Quarterfinal | Jake HumphreysWis.-Whitewater def. Andres SaenzGustavus Adolphus College | 6-4, 6-1 |
| Semifinal | Mohanad Al HouniGustavus Adolphus College def. Zack EksteinGustavus Adolphus College | 6-2, 6-4 |
| Semifinal | Brady AndersonCoe College def. Jake HumphreysWis.-Whitewater | 2-6, 6-3, 6-1 |
| Final | Mohanad Al HouniGustavus Adolphus College def. Brady AndersonCoe College | 6-2, 6-2 |
