| Round of 128 | Nick AneyGustavus Adolphus def. Daniel PerezSaint John's University | 6-0, 6-1 |
| Round of 128 | Landon SatherConcordia Wisconsin def. Gergo Potz NagyUW-Superior | 6-3, 6-3 |
| Round of 128 | Bo WilsonCoe def. Will WalshCarleton College | 6-4, 6-3 |
| Round of 128 | W Giacomo LucchesiSt. Scholastica def. Evan HuemoellerSaint Mary's University | 7-5, 4-6, 10-7 |
| Round of 128 | Daniel MooreCarthage def. Joaquim FernandesLuther College | 6-2, 6-3 |
| Round of 128 | Luke HaddorffGustavus Adolphus def. William StepanskiCarleton College | 6-3, 6-3 |
| Round of 128 | Josh ChristensenGustavus Adolphus def. Demitri BushUW-Eau Claire | 6-2, 6-1 |
| Round of 128 | Henry BridgersGrinnell def. Payton AdkissonWis.-Whitewater | 7-5, 6-1 |
| Round of 128 | John ZakowskiWis.-Whitewater def. Jordan DoiMacalester | 6-1, 6-1 |
| Round of 128 | John FoleyUW-Eau Claire def. Mark RosenSaint John's University | 6-0, 6-1 |
| Round of 128 | Justin SehlinGustavus Adolphus def. Eli YoungLuther College | 6-1, 6-2 |
| Round of 128 | Aiden KlassGrinnell def. Tommy LinkenheldLoras College | 6-3, 6-0 |
| Round of 128 | Alex BuddeGustavus Adolphus def. Jordan OaksCoe | 6-1, 6-3 |
| Round of 128 | Aswath ViswanathanCarleton College def. Nick MarinoCarthage | 6-3, 7-6 |
| Round of 128 | Bowen MinceGrinnell def. Josh BaldwinWis.-Whitewater | 4-6, 6-1, 10-4 |
| Round of 128 | Jason ReillyBethel (MN) def. Grant CountsUW-La Crosse | 6-1, 6-2 |
| Round of 128 | Nyathi MotlojoaLuther College def. Sam ThompsonHamline | 6-0, 6-4 |
| Round of 128 | Taona MhwandagaraGustavus Adolphus def. Stewart MorrellNorthwestern-St. Paul | 6-1, 6-0 |
| Round of 128 | Yuv KatariaCarleton College def. Jacob ZachariasUW-Superior | 6-0, 6-0 |
| Round of 128 | Jacob LukkarilaBethel (MN) def. Lorenzo CazzamaliSt. Olaf College | by default |
| Round of 128 | Marco SivieroGustavus Adolphus def. Parker HearneWis.-Whitewater | 6-2, 6-1 |
| Round of 128 | Sam RudenbergGrinnell def. Nicolas WelkerCarthage | 6-1, 6-1 |
| Round of 128 | Matt ChristensenUW-Eau Claire def. Wil McDowellSaint John's University | 6-4, 7-5 |
| Round of 128 | Cole ContardiUW-La Crosse def. Tim PetersConcordia Wisconsin | 6-4, 6-3 |
| Round of 128 | W Elliot SchneiderSt. Scholastica def. Anton KorolevMacalester | 7-6, 6-3 |
| Round of 128 | Drew ElofsonGustavus Adolphus def. Noah GuillermoWis.-Whitewater | 6-3, 6-1 |
| Round of 128 | Jack BergmeyerGustavus Adolphus def. Cooper FerruzziCarthage | 6-4, 6-3 |
| Round of 128 | Tate FullerCarleton College def. Paul ElghouayelGrinnell | 6-3, 6-0 |
| Round of 128 | Ryan MitchellWis.-Whitewater def. Tanner FinkenCentral | 6-0, 6-2 |
| Round of 128 | Chris MitevCarthage def. Trevor SmileySaint Mary's University | 6-0, 6-0 |
| Round of 128 | Jon LansingCoe def. Lucas HuffmanWartburg | 6-4, 6-2 |
| Round of 128 | Sourabh TerakanambiGustavus Adolphus def. Evan SadowskiWisconsin Lutheran | 3-6, 6-3, 10-6 |
| Round of 128 | Noah MuellerCarleton College def. Josh JanssenSaint Mary's University | 6-2, 6-1 |
| Round of 128 | L Myles KrzewinskiCarthage def. Riley VersichSt. Scholastica | 6-0, 6-0 |
| Round of 128 | Noah WankerlWis.-Whitewater def. Nathan MeskellCoe | 6-2, 6-2 |
| Round of 128 | Caleb FridingerGustavus Adolphus def. Wilder CookeGrinnell | 6-3, 6-2 |
| Round of 128 | Trey MelvinCentral def. Peter NaylorConcordia Wisconsin | 6-2, 6-2 |
| Round of 128 | Spencer SkidmoreGrinnell def. Max LoenLuther College | 6-2, 6-2 |
| Round of 128 | Richard GriffithsUW-Eau Claire def. Aidan NewbergWisconsin Lutheran | 6-0, 6-0 |
| Round of 128 | Rafael CostaGustavus Adolphus def. Alex GrayWis.-Whitewater | 7-5, 6-0 |
| Round of 128 | Kevin BlomquistLoras College def. Hayden FrieseCarthage | by default |
| Round of 128 | Diego GuzmanGustavus Adolphus def. Karsten KnutsenMacalester | 6-2, 6-7, 10-4 |
| Round of 128 | Graham PetersonCoe def. Eian CoadLoras College | 6-0, 6-4 |
| Round of 128 | Tarm RojanasoonthonCarleton College def. Noah GuillermoWis.-Whitewater | 5-7, 6-1, 10-5 |
| Round of 128 | Erik BeckersBethel (MN) def. Ethan BruhaSt. Olaf College | 6-1, 6-3 |
| Round of 128 | Leonard EsztergomiGrinnell def. Peyton FischerSaint John's University | 7-5, 6-3 |
| Round of 128 | Cade DavisWartburg def. Michael JanesUW-Superior | 6-1, 6-1, 11-9 |
| Round of 128 | Indraneel RautGustavus Adolphus def. Alex MooreUW-La Crosse | 6-0, 6-2 |
| Round of 128 | L Karch KnollGrinnell def. Jonas AbeledaSt. Scholastica | 7-5, 6-3 |
| Round of 128 | Joseph PunnooseGustavus Adolphus def. Brendan PietilaWis.-Whitewater | 3-6, 6-2, 10-5 |
| Round of 128 | Logan SnyderConcordia Wisconsin def. Brad DiLeoCentral | 6-4, 6-2 |
| Round of 128 | Hunter RosethUW-Eau Claire def. Jackson EelsWartburg | 6-1, 6-2 |
| Round of 128 | Jorge MeloLuther College def. Matthew SullivanMacalester | 7-5, 7-5 |
| Round of 128 | Xander RotiCarleton College def. Ridley ArandaWis.-Whitewater | 6-3, 6-1 |
| Round of 128 | Tripp SchulteCarthage def. Will DetersSaint John's University | 6-3, 6-2 |
| Round of 128 | Daniel FouchierGustavus Adolphus def. Simon KennelGrinnell | 6-1, 6-0 |
| Round of 128 | Jonah GilmoreGrinnell def. Brandon KurillaSaint Mary's University | 6-1, 6-0 |
| Round of 128 | Federico FiordaGustavus Adolphus def. Luke WestholderLuther College | 7-5, 6-3 |
| Round of 128 | Sean BochmanGustavus Adolphus def. Sho TanakaCarleton College | 7-6, 6-3 |
| Round of 128 | Cole LindwallWis.-Whitewater def. Tim RobackSt. Olaf College | 6-0, 6-1 |
| Round of 128 | Andre GuedesUW-Superior def. Riley CollinsLoras College | 6-2, 6-1 |
| Round of 128 | Oscar WikstromGustavus Adolphus def. Hunter FischerSaint John's University | 6-0, 6-0 |
| Round of 128 | Aniketh VipparalaCarleton College def. Alex SargentMacalester | 6-2, 6-4 |
| Round of 128 | Yanozie AmadikeCarthage def. Remi HemaidanCoe | 6-3, 7-6 |
| Round of 64 | Nick AneyGustavus Adolphus def. Landon SatherConcordia Wisconsin | 6-1, 7-5 |
| Round of 64 | L Bo WilsonCoe def. Giacomo LucchesiSt. Scholastica | 6-0, 6-3 |
| Round of 64 | Daniel MooreCarthage def. Luke HaddorffGustavus Adolphus | 6-4, 6-3 |
| Round of 64 | Josh ChristensenGustavus Adolphus def. Henry BridgersGrinnell | 6-0, 6-1 |
| Round of 64 | John ZakowskiWis.-Whitewater def. John FoleyUW-Eau Claire | 3-6, 6-3, 10-7 |
| Round of 64 | Justin SehlinGustavus Adolphus def. Aiden KlassGrinnell | 6-2, 6-1 |
| Round of 64 | Alex BuddeGustavus Adolphus def. Aswath ViswanathanCarleton College | 7-5, 6-3 |
| Round of 64 | Bowen MinceGrinnell def. Jason ReillyBethel (MN) | 6-2, 6-3 |
| Round of 64 | Nyathi MotlojoaLuther College def. Taona MhwandagaraGustavus Adolphus | 7-5, 5-7, 10-3 |
| Round of 64 | Yuv KatariaCarleton College def. Jacob LukkarilaBethel (MN) | 6-2, 6-0 |
| Round of 64 | Marco SivieroGustavus Adolphus def. Sam RudenbergGrinnell | 2-6, 6-2, 10-3 |
| Round of 64 | Matt ChristensenUW-Eau Claire def. Cole ContardiUW-La Crosse | 6-2, 6-3 |
| Round of 64 | L Drew ElofsonGustavus Adolphus def. Elliot SchneiderSt. Scholastica | 6-2, 7-5 |
| Round of 64 | Tate FullerCarleton College def. Jack BergmeyerGustavus Adolphus | 7-5, 6-4 |
| Round of 64 | Ryan MitchellWis.-Whitewater def. Chris MitevCarthage | 6-0, 6-3 |
| Round of 64 | Jon LansingCoe def. Sourabh TerakanambiGustavus Adolphus | 3-6, 6-3, 11-9 |
| Round of 64 | Myles KrzewinskiCarthage def. Noah MuellerCarleton College | 6-3, 6-1 |
| Round of 64 | Caleb FridingerGustavus Adolphus def. Noah WankerlWis.-Whitewater | 6-2, 6-1 |
| Round of 64 | Max LoenLuther College def. Trey MelvinCentral | 6-3, 6-2 |
| Round of 64 | Rafael CostaGustavus Adolphus def. Richard GriffithsUW-Eau Claire | 6-4, 6-2 |
| Round of 64 | Diego GuzmanGustavus Adolphus def. Kevin BlomquistLoras College | 6-1, 6-1 |
| Round of 64 | Tarm RojanasoonthonCarleton College def. Graham PetersonCoe | 6-0, 6-2 |
| Round of 64 | Leonard EsztergomiGrinnell def. Erik BeckersBethel (MN) | 6-3, 6-4 |
| Round of 64 | Indraneel RautGustavus Adolphus def. Cade DavisWartburg | 6-1, 6-0 |
| Round of 64 | Karch KnollGrinnell def. Joseph PunnooseGustavus Adolphus | 6-4, 6-2 |
| Round of 64 | Hunter RosethUW-Eau Claire def. Logan SnyderConcordia Wisconsin | 6-1, 6-1 |
| Round of 64 | Xander RotiCarleton College def. Jorge MeloLuther College | 6-3, 6-1 |
| Round of 64 | Daniel FouchierGustavus Adolphus def. Tripp SchulteCarthage | 6-2, 6-0 |
| Round of 64 | Federico FiordaGustavus Adolphus def. Jonah GilmoreGrinnell | 6-2, 6-0 |
| Round of 64 | Cole LindwallWis.-Whitewater def. Sean BochmanGustavus Adolphus | 6-3, 6-3 |
| Round of 64 | Oscar WikstromGustavus Adolphus def. Andre GuedesUW-Superior | 6-3, 6-2 |
| Round of 64 | Yanozie AmadikeCarthage def. Aniketh VipparalaCarleton College | 6-3, 6-0 |
| Round of 32 | Nick AneyGustavus Adolphus def. Bo WilsonCoe | 6-1, 6-4 |
| Round of 32 | Josh ChristensenGustavus Adolphus def. Daniel MooreCarthage | 6-2, 6-1 |
| Round of 32 | John ZakowskiWis.-Whitewater def. Justin SehlinGustavus Adolphus | 6-3, 6-2 |
| Round of 32 | Bowen MinceGrinnell def. Alex BuddeGustavus Adolphus | 6-3, 1-6, 10-7 |
| Round of 32 | Nyathi MotlojoaLuther College def. Yuv KatariaCarleton College | 6-1, 6-4 |
| Round of 32 | Marco SivieroGustavus Adolphus def. Matt ChristensenUW-Eau Claire | 6-2, 6-2 |
| Round of 32 | Drew ElofsonGustavus Adolphus def. Tate FullerCarleton College | 6-4, 6-3 |
| Round of 32 | Jon LansingCoe def. Ryan MitchellWis.-Whitewater | 6-7, 7-6, 10-4 |
| Round of 32 | Caleb FridingerGustavus Adolphus def. Myles KrzewinskiCarthage | 6-1, 6-2 |
| Round of 32 | Rafael CostaGustavus Adolphus def. Max LoenLuther College | 7-5, 6-1 |
| Round of 32 | Tarm RojanasoonthonCarleton College def. Diego GuzmanGustavus Adolphus | 6-4, 6-2 |
| Round of 32 | Indraneel RautGustavus Adolphus def. Leonard EsztergomiGrinnell | 6-4, 6-1 |
| Round of 32 | Karch KnollGrinnell def. Hunter RosethUW-Eau Claire | 6-3, 2-6, 10-6 |
| Round of 32 | Daniel FouchierGustavus Adolphus def. Xander RotiCarleton College | 3-6, 6-1, 10-3 |
| Round of 32 | Cole LindwallWis.-Whitewater def. Federico FiordaGustavus Adolphus | 6-3, 6-3 |
| Round of 32 | Oscar WikstromGustavus Adolphus def. Yanozie AmadikeCarthage | 6-2, 6-3 |
| Round of 16 | Nick AneyGustavus Adolphus def. Josh ChristensenGustavus Adolphus | 7-6, 1-6, 10-8 |
| Round of 16 | John ZakowskiWis.-Whitewater def. Bowen MinceGrinnell | 2-6, 6-2, 10-7 |
| Round of 16 | Nyathi MotlojoaLuther College def. Marco SivieroGustavus Adolphus | 7-5, 7-5 |
| Round of 16 | Drew ElofsonGustavus Adolphus def. Jon LansingCoe | 6-2, 6-4 |
| Round of 16 | Caleb FridingerGustavus Adolphus def. Rafael CostaGustavus Adolphus | 7-5, 7-5 |
| Round of 16 | Indraneel RautGustavus Adolphus def. Tarm RojanasoonthonCarleton College | 7-5, 6-3 |
| Round of 16 | Daniel FouchierGustavus Adolphus def. Karch KnollGrinnell | 3-6, 6-1, 10-3 |
| Round of 16 | Cole LindwallWis.-Whitewater def. Oscar WikstromGustavus Adolphus | 6-4, 6-4 |
| Quarterfinal | John ZakowskiWis.-Whitewater def. Nick AneyGustavus Adolphus | 6-3, 6-4 |
| Quarterfinal | Drew ElofsonGustavus Adolphus def. Marco SivieroGustavus Adolphus | 4-6, 6-3, 10-7 |
| Quarterfinal | Indraneel RautGustavus Adolphus def. Caleb FridingerGustavus Adolphus | 6-2, 6-3 |
| Quarterfinal | Cole LindwallWis.-Whitewater def. Daniel FouchierGustavus Adolphus | 6-7, 6-4, 14-12 |
| Semifinal | John ZakowskiWis.-Whitewater def. Drew ElofsonGustavus Adolphus | 6-4, 6-2 |
| Semifinal | Cole LindwallWis.-Whitewater def. Indraneel RautGustavus Adolphus | 6-3, 2-6, 10-3 |
| Final | John ZakowskiWis.-Whitewater def. Cole LindwallWis.-Whitewater | 4-6, 6-4, 10-5 |
