| Round of 128 | Eric WollumUW-Eau Claire vs. Bye | no result |
| Round of 128 | Charlie ReinerstenSt. Olaf def. Josh SandeGustavus Adolphus | 6-2, 6-3 |
| Round of 128 | Travis MurphyUW-La Crosse def. Abhay NadipuramWartburg | 6-1, 6-1 |
| Round of 128 | Logan CovelliUW-Whitewater vs. Bye | no result |
| Round of 128 | L Tucker MorrisBethel def. Alex NagleSt. Scholastica | 6-1, 6-0 |
| Round of 128 | Thao LorConcordia University vs. Bye | no result |
| Round of 128 | Tyler Van HeestLuther def. Jerald MackeySt. Thomas | 4-6, 6-4, 10-4 |
| Round of 128 | Brian HolmgrenSaint John's vs. Bye | no result |
| Round of 128 | Nick AcostaSt. Norbert vs. Bye | no result |
| Round of 128 | Ben RobertsonUW-Eau Claire def. Talor CurtisSaint John's | 6-4, 6-4 |
| Round of 128 | Zach WeaverMilwaukee School of Engineerin vs. Bye | no result |
| Round of 128 | Will MitchellSt. Olaf def. Dave BloomquistConcordia College | 6-1, 6-3 |
| Round of 128 | Justin LoefflerSaint Mary's vs. Bye | no result |
| Round of 128 | Austin TaylorCarleton vs. Bye | no result |
| Round of 128 | Derek TaylorUW-Whitewater def. Chris MattesonDubuque | 6-2, 6-1 |
| Round of 128 | vs. Jared LevyLoras | no result |
| Round of 128 | Mark SchadlerMilwaukee School of Engineerin vs. Bye | no result |
| Round of 128 | Bryce JohnsonBethel def. Cameron GaskinConcordia University | 6-1, 6-1 |
| Round of 128 | Jon FossSt. Olaf vs. Bye | no result |
| Round of 128 | Devon LarsonConcordia College def. Erik HermensonSt. Thomas | 4-6, 6-1, 11-9 |
| Round of 128 | Justin LeBeauxSaint John's vs. Bye | no result |
| Round of 128 | Pat PisaniGustavus Adolphus def. Brendan FitzPatrickHamline | 6-2, 6-2 |
| Round of 128 | Mark SansaitUW-Whitewater vs. Bye | no result |
| Round of 128 | Kai PetersonMacalester vs. Bye | no result |
| Round of 128 | Chris BuckinghamWartburg def. Jared LevyDubuque | by default |
| Round of 128 | Paul CooperCarleton def. Demetrius JohnsonDubuque | 6-2, 7-6 (0-4) |
| Round of 128 | David StingleyUW-Eau Claire vs. Bye | no result |
| Round of 128 | L Charlie MillerUW-Whitewater def. Tucker CombsSt. Scholastica | 6-1, 6-2 |
| Round of 128 | Dustin HolzhauerMilwaukee School of Engineerin vs. Bye | no result |
| Round of 128 | Chase KrebsbachLuther def. Brian OlsonConcordia College | 6-4, 6-4 |
| Round of 128 | Connor IlliesGustavus Adolphus vs. Bye | no result |
| Round of 128 | Alex KakerUW-La Crosse vs. Bye | no result |
| Round of 128 | Nate JungLuther vs. Bye | no result |
| Round of 128 | Jake ThompsonConcordia College vs. Bye | no result |
| Round of 128 | Matt HallstromBethel def. Brandon StensethUW-La Crosse | 6-4, 6-4 |
| Round of 128 | RJ RademacherUW-Whitewater vs. Bye | no result |
| Round of 128 | Brooks StapletonGustavus Adolphus vs. Bye | no result |
| Round of 128 | Dirk Van RybroekUW-Eau Claire def. Bobby SteingreaberSaint Mary's | 6-2, 4-6, 10-5 |
| Round of 128 | Anthony BarhouseMilwaukee School of Engineerin vs. Bye | no result |
| Round of 128 | Jon ArandaCarleton vs. Bye | no result |
| Round of 128 | Braden JohnsonSt. Thomas vs. Bye | no result |
| Round of 128 | Joe McDevittSt. Olaf def. Andrew OhlandMilwaukee School of Engineerin | 6-2, 6-7 (0-5), 10-5 |
| Round of 128 | Chris CraigConcordia University vs. Bye | no result |
| Round of 128 | John BurnsSaint John's vs. Bye | no result |
| Round of 128 | Brady PorterUW-Whitewater def. Michael LiebermanGustavus Adolphus | 7-5, 0-6, 10-4 |
| Round of 128 | Kolin DeanSt. Scholastica vs. Bye | no result |
| Round of 128 | Reggie RonningBethel def. John KrollDubuque | 6-2, 6-1 |
| Round of 128 | Brian RasmussenWartburg vs. Bye | no result |
| Round of 128 | David JacobsenDubuque vs. Bye | no result |
| Round of 128 | Chris ThorntonUW-Eau Claire def. Andrew RangistchSaint Mary's | 6-1, 6-0 |
| Round of 128 | Will KriegerUW-Whitewater def. Sean GoldenGustavus Adolphus | 6-3, 6-1 |
| Round of 128 | L Krishna VegeCarleton def. Brian LindbergSt. Scholastica | 6-1, 7-5 |
| Round of 128 | Andy CataniaSt. Olaf vs. Bye | no result |
| Round of 128 | Matt PeckskampSaint John's def. TAylor ShafferConcordia University | 6-1, 6-2 |
| Round of 128 | Dan CromwellHamline def. Aaron MastersonWartburg | 6-4, 6-2 |
| Round of 128 | Jake ReitzLuther vs. Bye | no result |
| Round of 128 | Bye vs. Jordan LeFebvreBethel | no result |
| Round of 128 | Jacob StickneySt. Thomas vs. Bye | no result |
| Round of 128 | Chris VoigtSaint John's vs. Bye | no result |
| Round of 128 | Rodrigo OteroGustavus Adolphus def. Juan MontenegroMilwaukee School of Engineerin | 6-1, 6-2 |
| Round of 128 | Bryn HomuthConcordia College def. Rishab SachdevaUW-La Crosse | 2-6, 7-5, 10-7 |
| Round of 128 | Ben SchwartzUW-Whitewater vs. Bye | no result |
| Round of 128 | Aaron HauserConcordia University vs. Bye | no result |
| Round of 128 | Nick Hubbard-PetersSt. Olaf vs. Bye | no result |
| Round of 64 | Eric WollumUW-Eau Claire def. Charlie ReinertsenSt. Olaf | 4-6, 7-5, 10-5 |
| Round of 64 | Logan CovelliUW-Whitewater def. Travis MurphyUW-La Crosse | 6-2, 6-0 |
| Round of 64 | Tucker MorrisBethel def. Thao LorConcordia University | 6-2, 6-1 |
| Round of 64 | Tyler Van HeestLuther def. Brian HolmgrenSaint John's | 6-1, 6-1 |
| Round of 64 | Ben RobertsonUW-Eau Claire def. Nick AcostaSt. Norbert | 6-2, 7-5 |
| Round of 64 | Zach WeaverMilwaukee School of Engineerin vs. Will MitchellSt. Olaf | no result |
| Round of 64 | Austin TaylorCarleton def. Justin LoefflerSaint Mary's | 6-2, 6-2 |
| Round of 64 | Derek TaylorUW-Whitewater def. Jared LevyLoras | 6-2, 6-2 |
| Round of 64 | Bryce JohnsonBethel def. Mark SchadlerMilwaukee School of Engineerin | 6-1, 6-2 |
| Round of 64 | Jon FossSt. Olaf def. Devon LarsonConcordia College | 6-0, 6-2 |
| Round of 64 | Justin LeBeauxSaint John's vs. Pat PisaniGustavus Adolphus | 6-1, 6-7 (2-0) |
| Round of 64 | Mark SansaitUW-Whitewater def. Kai PetersonMacalester | 6-0, 6-0 |
| Round of 64 | Paul CooperCarleton def. Chris BuckinghamWartburg | 4-6, 6-3, 10-6 |
| Round of 64 | David StingleyUW-Eau Claire def. Charlie MillerUW-Whitewater | 6-2, 7-5 |
| Round of 64 | Chase KrebsbachLuther def. Dustin HolzhauerMilwaukee School of Engineerin | 6-2, 6-0 |
| Round of 64 | Connor IlliesGustavus Adolphus def. Alex KakerUW-La Crosse | 6-2, 7-6 (0-3) |
| Round of 64 | Nate JungLuther def. Jake ThompsonConcordia College | 6-2, 6-3 |
| Round of 64 | RJ RademacherUW-Whitewater def. Matt HallstromBethel | 6-2, 6-3 |
| Round of 64 | Brooks StapletonGustavus Adolphus def. Dirk VanRybroekUW-Eau Claire | 4-6, 6-4, 10-9 |
| Round of 64 | John ArandaCarleton def. Anthony BarhouseMilwaukee School of Engineerin | 6-0, 6-0 |
| Round of 64 | Braden JohnsonSt. Thomas def. Joe McDevittSt. Olaf | 7-5, 6-4 |
| Round of 64 | John BurnsSaint John's def. Chris CraigConcordia University | 6-0, 6-0 |
| Round of 64 | L Brady PorterUW-Whitewater def. Kolin DeanSt. Scholastica | 6-2, 6-0 |
| Round of 64 | Brian RasmussenWartburg def. Reggie RonningBethel | 6-1, 6-4 |
| Round of 64 | David JacobsenDubuque def. Chris ThorntonUW-Eau Claire | 6-3, 4-6, 10-8 |
| Round of 64 | Krishna VegeCarleton def. Will KriegerUW-Whitewater | 6-2, 6-4 |
| Round of 64 | Andy CataniaSt. Olaf def. Matt PeckskampSaint John's | 6-2, 6-0 |
| Round of 64 | Jake ReitzLuther def. Dan CromwellHamline | 6-2, 6-0 |
| Round of 64 | Jordan LeFebvreBethel vs. Jacob StickneySt. Thomas | no result |
| Round of 64 | Rodrigo OteroGustavus Adolphus def. Chris VoigtSaint John's | 7-5, 6-4 |
| Round of 64 | Ben SchwartzUW-Whitewater def. Bryn HomuthConcordia College | 6-1, 7-5 |
| Round of 64 | Nick Hubbard-PetersSt. Olaf def. Aaron HauserConcordia University | 6-0, 6-1 |
| Round of 32 | Eric WollumUW-Eau Claire def. Logan CovelliUW-Whitewater | 6-1, 6-3 |
| Round of 32 | Tucker MorrisBethel def. Tyler Van HeestLuther | 6-3, 6-4 |
| Round of 32 | Ben RobertsonUW-Eau Claire def. Will MitchellSt. Olaf | 2-6, 6-2, 10-0 |
| Round of 32 | Derek TaylorUW-Whitewater def. Austin TaylorCarleton | 6-0, 6-4 |
| Round of 32 | Jon FossSt. Olaf def. Bryce JohnsonBethel | 6-0, 6-4 |
| Round of 32 | Mark SansaitUW-Whitewater def. Pat PisaniGustavus Adolphus | 6-1, 6-2 |
| Round of 32 | Paul CooperCarleton def. David StingleyUW-Eau Claire | 6-3, 6-4 |
| Round of 32 | Connor IlliesGustavus Adolphus def. Chase KrebsbachLuther | 6-4, 7-6 (0-5) |
| Round of 32 | RJ RademacherUW-Whitewater def. Nate JungLuther | 3-6, 6-1, 10-5 |
| Round of 32 | John ArandaCarleton def. Brooks StapletonGustavus Adolphus | 6-4, 6-3 |
| Round of 32 | Braden JohnsonSt. Thomas def. John BurnsSaint John's | 6-2, 6-3 |
| Round of 32 | Brady PorterUW-Whitewater def. Brian RasmussenWartburg | 6-1, 6-0 |
| Round of 32 | Krishna VegeCarleton def. David JacobsenDubuque | 4-6, 6-4, 10-5 |
| Round of 32 | Andy CataniaSt. Olaf def. Jake ReitzLuther | 6-3, 6-1 |
| Round of 32 | Jacob StickneySt. Thomas def. Rodrigo OteroGustavus Adolphus | 7-5, 6-3 |
| Round of 32 | Ben SchwartzUW-Whitewater def. Nick Hubbard-PetersSt. Olaf | 6-4, 6-3 |
| Round of 16 | Tucker MorrisBethel def. Eric WollumUW-Eau Claire | 7-6 (0-5), 6-4 |
| Round of 16 | Derek TaylorUW-Whitewater def. Ben RobertsonUW-Eau Claire | 7-5, 6-4 |
| Round of 16 | Mark SansaitUW-Whitewater def. Jon FossSt. Olaf | 6-3, 6-1 |
| Round of 16 | Paul CooperCarleton def. Connor IlliesGustavus Adolphus | 7-5, 2-6, 10-7 |
| Round of 16 | RJ RademacherUW-Whitewater def. John ArandaCarleton | 6-4, 3-6, 10-3 |
| Round of 16 | Braden JohnsonSt. Thomas def. Brady PorterUW-Whitewater | 1-6, 6-4, 10-8 |
| Round of 16 | Krishna VegeCarleton def. Andy CataniaSt. Olaf | 6-1, 7-6 (0-4) |
| Round of 16 | Ben SchwartzUW-Whitewater def. Jacob StickneySt. Thomas | 6-3, 6-1 |
| Quarterfinal | Tucker MorrisBethel def. Derek TaylorUW-Whitewater | 6-3, 7-6 (0-6) |
| Quarterfinal | Paul CooperCarleton def. Mark SansaitUW-Whitewater | 4-6, 6-3, 10-5 |
| Quarterfinal | RJ RademacherUW-Whitewater def. Braden JohnsonSt. Thomas | 6-4, 6-3 |
| Quarterfinal | Ben SchwartzUW-Whitewater def. Krishna VegeCarleton | 6-3, 6-4 |
| Semifinal | Tucker MorrisBethel def. Paul CooperCarleton | 7-6 (0-5), 5-7, 10-7 |
| Semifinal | RJ RademacherUW-Whitewater def. Ben SchwartzUW-Whitewater | 3-6, 7-6 (0-4), 10-6 |
| Final | Tucker MorrisBethel def. RJ RademacherUW-Whitewater | 6-0, 7-5 |
