| Round of 128 | Joel HugGustavus Adolphus def. Henry JohnsonGrinnell College | 6-1, 6-1 |
| Round of 128 | Matt KrzewinskiCarthage College def. Tanner FinkenCentral | 6-4, 6-5 |
| Round of 128 | Cole WerningConcordia-Wisconsin def. Tou Ger XiongHamline | 6-4, 6-5 |
| Round of 128 | Alex MooreUW-La Crosse def. Wil McDowellSaint John's University | 6-4, 4-6, 7-5 |
| Round of 128 | Suyash GuptaGustavus Adolphus def. Erik BeckersBethel University | 6-3, 6-3 |
| Round of 128 | Matthew SullivanMacalester def. Axel FigueroaDubuque, Univ. of | 6-2, 6-0 |
| Round of 128 | Jon LansingCoe College def. Tanner LundbergConcordia-Moorhead | 3-6, 6-2, 6-0 |
| Round of 128 | John NykyforukCarthage College def. Sterling SibleySt. Thomas | 6-4, 6-4 |
| Round of 128 | Lewis WhiteCarleton College def. Robert RiderWis.-Whitewater | 4-6, 6-0, 6-3 |
| Round of 128 | Ishaan TibrewalGrinnell College def. Justin SehlinGustavus Adolphus | 6-4, 6-4 |
| Round of 128 | Nathan MeskellCoe College def. Brandon KurillaSaint Mary's University | 6-1, 6-2 |
| Round of 128 | Jason ReillyBethel University def. Logan SnyderConcordia-Wisconsin | 6-2, 7-6 |
| Round of 128 | Tripp SchulteCarthage College def. Jonas Lindholm-UzziCarleton College | 7-6, 6-4 |
| Round of 128 | Erik PorterConcordia-Moorhead def. Zach LaveneSt. Thomas | 2-6, 6-1, 6-0 |
| Round of 128 | Drew ElofsonGustavus Adolphus def. Adam BurkeGrinnell College | 6-3, 6-3 |
| Round of 128 | Lawrence HiquianaGustavus Adolphus def. Nick VossenSt. Thomas | 6-2, 6-0 |
| Round of 128 | William StepanskiCarleton College def. Zach WoodWis.-Whitewater | 6-2, 2-6, 6-3 |
| Round of 128 | Grant MautheEau Claire Men's Tennis def. Brad DiLeoCentral | 6-1, 6-1 |
| Round of 128 | Lucas NayCarroll College def. Hayden FrieseCarthage College | 6-2, 6-1 |
| Round of 128 | Spencer WickSt. Olaf def. Tony MooreUW-La Crosse | 6-4, 3-6, 6-1 |
| Round of 128 | Nazeer RobinsonHamline def. Carter SteffesConcordia-Moorhead | 6-4, 7-6 |
| Round of 128 | Jordan SchenckSt. Thomas def. Gabe BinversieConcordia-Wisconsin | 6-1, 7-5 |
| Round of 128 | Bo WilsonCoe College def. Riley PetersonUW-La Crosse | 6-7, 6-1, 6-2 |
| Round of 128 | W Elliot SchneiderSt. Scholastica def. Patrick AndersonCarthage College | 6-0, 6-2 |
| Round of 128 | Aswhath ViswanathanCarleton College def. Mouaad AlhouniGustavus Adolphus | 6-2, 3-6, 7-5 |
| Round of 128 | Jared SaueConcordia-Moorhead def. Brook NorwoodLuther College | 6-1, 7-5 |
| Round of 128 | Alex BuddeGustavus Adolphus def. Zach JanssenEau Claire Men's Tennis | 6-2, 6-4 |
| Round of 128 | William IsimingerCentral def. Kevin BlomquistLoras College | 6-4, 6-2 |
| Round of 128 | Anton KorolevMacalester def. Andre AntressianCarthage College | 6-1, 6-7, 7-5 |
| Round of 128 | Lucas HuffmanWartburg College def. Shoma KishimotoCornell College | 6-2, 6-0 |
| Round of 128 | Noah GuillermoWis.-Whitewater def. Jack BergmeyerGustavus Adolphus | 6-2, 6-0 |
| Round of 128 | L Brendan PietilaWis.-Whitewater def. Rafa GonzalezSt. Scholastica | 6-4, 6-2 |
| Round of 128 | Tristan FjelstadSt. Thomas def. Ben SwansonConcordia-Moorhead | by default |
| Round of 128 | Xavier SangaGustavus Adolphus def. Zach KantorBethel University | 6-1, 6-4 |
| Round of 128 | Jose MancillaDubuque, Univ. of def. Alec RudhSaint Mary's University | 3-6, 6-3, 6-2 |
| Round of 128 | Hunter RosethEau Claire Men's Tennis def. Jack LunnGrinnell College | 6-3, 6-2 |
| Round of 128 | Cole LindwallWis.-Whitewater def. Joe HarrisonCarroll College | 6-2, 6-3 |
| Round of 128 | Nolan RademacherConcordia-Wisconsin def. Ethan St. JohnCentral | 6-0, 6-0 |
| Round of 128 | Sourabh TerakanambiGustavus Adolphus def. Karsten KnutsenMacalester | 6-3, 6-1 |
| Round of 128 | Tyler NelsonCoe College def. Erick NussSt. Thomas | 6-3, 6-4 |
| Round of 128 | George KaslowGrinnell College def. Zizi AmadikeCarthage College | 6-1, 6-3 |
| Round of 64 | Leo VithoontienCarleton College def. Joel HugGustavus Adolphus | 6-0, 6-1 |
| Round of 64 | W Serhii TykhonenkoSt. Scholastica def. Matt KrzewinskiCarthage College | 6-3, 6-2 |
| Round of 64 | Danila BorovykhWis.-Whitewater def. Cole WerningConcordia-Wisconsin | 6-0, 6-0 |
| Round of 64 | Suyash GuptaGustavus Adolphus def. Alex MooreUW-La Crosse | 6-2, 3-6, 6-2 |
| Round of 64 | Michael O'NeilGustavus Adolphus def. Matthew SullivanMacalester | 6-0, 6-1 |
| Round of 64 | John NykyforukCarthage College def. Jon LansingCoe College | 6-4, 6-4 |
| Round of 64 | Grant MortonLuther College def. Lewis WhiteCarleton College | 6-0, 6-3 |
| Round of 64 | Matt ChristensenEau Claire Men's Tennis def. Ishaan TibrewalGrinnell College | 5-7, 6-3, 6-2 |
| Round of 64 | Nick AneyGustavus Adolphus def. Nathan MeskellCoe College | 6-2, 6-1 |
| Round of 64 | Jason ReillyBethel University def. Tripp SchulteCarthage College | 6-2, 6-2 |
| Round of 64 | Ryan MitchellWis.-Whitewater def. Erik PorterConcordia-Moorhead | 6-2, 6-2 |
| Round of 64 | Nyathi MotlojoaLuther College def. Drew ElofsonGustavus Adolphus | 6-7, 6-2, 6-1 |
| Round of 64 | Rami HemaidanCoe College def. Lawrence HiquianaGustavus Adolphus | 6-1, 6-1 |
| Round of 64 | Jeffrey JorgensenMacalester def. William StepanskiCarleton College | 6-4, 6-1 |
| Round of 64 | Daniel FouchierGustavus Adolphus def. Grant MautheEau Claire Men's Tennis | 6-2, 7-6 |
| Round of 64 | Spencer WickSt. Olaf def. Lucas NayCarroll College | 6-4, 7-6 |
| Round of 64 | Nate JordreSaint John's University def. Nazeer RobinsonHamline | 6-1, 6-1 |
| Round of 64 | Indraneel RautGustavus Adolphus def. Jordan SchenckSt. Thomas | 6-4, 6-3 |
| Round of 64 | W Elliot SchneiderSt. Scholastica def. Bo WilsonCoe College | 7-5, 6-2 |
| Round of 64 | Alex GrayWis.-Whitewater def. Aswhath ViswanathanCarleton College | 6-4, 6-0 |
| Round of 64 | Alex BuddeGustavus Adolphus def. Jared SaueConcordia-Moorhead | 6-2, 6-3 |
| Round of 64 | Bowen MinceGrinnell College def. William IsimingerCentral | 6-4, 6-3 |
| Round of 64 | Lucas HuffmanWartburg College def. Anton KorolevMacalester | 6-0, 3-6, 6-4 |
| Round of 64 | Varun IyerCarleton College def. Noah GuillermoWis.-Whitewater | 6-3, 6-1 |
| Round of 64 | Daniel MooreCarthage College def. Brendan PietilaWis.-Whitewater | 2-6, 6-4, 6-1 |
| Round of 64 | Joseph PunnooseGustavus Adolphus def. Tristan FjelstadSt. Thomas | 6-0, 6-2 |
| Round of 64 | Xavier SangaGustavus Adolphus def. Jose MancillaDubuque, Univ. of | 6-0, 6-1 |
| Round of 64 | Cole SchneiderLuther College def. Hunter RosethEau Claire Men's Tennis | 1-6, 7-6, 7-6 |
| Round of 64 | Cole LindwallWis.-Whitewater def. Nolan RademacherConcordia-Wisconsin | 6-4, 6-4 |
| Round of 64 | Alexander RotiCarleton College def. Sourabh TerakanambiGustavus Adolphus | 6-4, 6-1 |
| Round of 64 | Alex AltUW-La Crosse def. Tyler NelsonCoe College | 6-2, 6-4 |
| Round of 64 | Yassine DerbaniGustavus Adolphus def. George KaslowGrinnell College | 6-1, 6-1 |
| Round of 32 | L Leo VithoontienCarleton College def. Serhii TykhonenkoSt. Scholastica | 6-1, 6-3 |
| Round of 32 | Danila BorovykhWis.-Whitewater def. Suyash GuptaGustavus Adolphus | 6-3, 6-2 |
| Round of 32 | Michael O'NeilGustavus Adolphus def. Jon LansingCoe College | 6-2, 6-2 |
| Round of 32 | Matt ChristensenEau Claire Men's Tennis def. Grant MortonLuther College | 6-2, 6-3 |
| Round of 32 | Nick AneyGustavus Adolphus def. Jason ReillyBethel University | 7-5, 6-3 |
| Round of 32 | Ryan MitchellWis.-Whitewater def. Nyathi MotlojoaLuther College | 3-6, 6-4, 7-6 |
| Round of 32 | Rami HemaidanCoe College def. Jeffrey JorgensenMacalester | 6-2, 6-0 |
| Round of 32 | Daniel FouchierGustavus Adolphus def. Spencer WickSt. Olaf | 6-4, 6-2 |
| Round of 32 | Indraneel RautGustavus Adolphus def. Nate JordreSaint John's University | 6-4, 7-5 |
| Round of 32 | L Alex GrayWis.-Whitewater def. Elliot SchneiderSt. Scholastica | 6-1, 1-6, 6-4 |
| Round of 32 | Alex BuddeGustavus Adolphus def. Bowen MinceGrinnell College | 6-1, 6-4 |
| Round of 32 | Varun IyerCarleton College def. Lucas HuffmanWartburg College | 6-2, 6-1 |
| Round of 32 | Joseph PunnooseGustavus Adolphus def. Daniel MooreCarthage College | 6-4, 7-6 |
| Round of 32 | Cole SchneiderLuther College def. Xavier SangaGustavus Adolphus | 4-6, 6-4, 6-2 |
| Round of 32 | Alexander RotiCarleton College def. Cole LindwallWis.-Whitewater | 6-3, 1-6, 6-2 |
| Round of 32 | Yassine DerbaniGustavus Adolphus def. Alex AltUW-La Crosse | 6-1, 6-2 |
| Round of 16 | Leo VithoontienCarleton College def. Danila BorovykhWis.-Whitewater | 6-2, 6-4 |
| Round of 16 | Michael O'NeilGustavus Adolphus def. Matt ChristensenEau Claire Men's Tennis | 6-2, 6-2 |
| Round of 16 | Nick AneyGustavus Adolphus def. Ryan MitchellWis.-Whitewater | 6-1, 6-3 |
| Round of 16 | Daniel FouchierGustavus Adolphus def. Rami HemaidanCoe College | 6-0, 6-2 |
| Round of 16 | Indraneel RautGustavus Adolphus def. Alex GrayWis.-Whitewater | 6-2, 6-0 |
| Round of 16 | Varun IyerCarleton College def. Alex BuddeGustavus Adolphus | 6-3, 6-2 |
| Round of 16 | Cole SchneiderLuther College def. Joseph PunnooseGustavus Adolphus | 6-3, 2-6, 6-4 |
| Round of 16 | Yassine DerbaniGustavus Adolphus def. Alexander RotiCarleton College | 7-5, 6-3 |
| Quarterfinal | Leo VithoontienCarleton College def. Michael O'NeilGustavus Adolphus | 6-0, 6-2 |
| Quarterfinal | Nick AneyGustavus Adolphus def. Daniel FouchierGustavus Adolphus | 6-2, 6-4 |
| Quarterfinal | Indraneel RautGustavus Adolphus def. Varun IyerCarleton College | 6-3, 6-4 |
| Quarterfinal | Yassine DerbaniGustavus Adolphus def. Cole SchneiderLuther College | 0-6, 6-3, 6-4 |
| Semifinal | Leo VithoontienCarleton College def. Nick AneyGustavus Adolphus | 6-4, 6-3 |
| Semifinal | Indraneel RautGustavus Adolphus def. Yassine DerbaniGustavus Adolphus | 6-3, retired |
| Final | Leo VithoontienCarleton College def. Indraneel RautGustavus Adolphus | 6-2, 6-1 |
