| Round of 128 | Mike GreenbergKenyon vs. Bye | no result |
| Round of 128 | Nick LehnertAugustana def. Nick BoomgardenCarthage | 6-2, 6-2 |
| Round of 128 | Joey Van LieshoutUW-La Crosse def. Kyle TuckerCoe College | 6-3, 6-3 |
| Round of 128 | Daniel NellisGrinnell def. Peter MohrLawerence | 6-0, 6-0 |
| Round of 128 | Robert BeckerHU def. Max BuschLuther | 6-4, 3-6, 10-5 |
| Round of 128 | Max EdwardsMacalester def. Matt LobeckSt. Norbert College | 7-5, 6-1 |
| Round of 128 | James LewisonUW-Oshkosh def. Daniel PomerancGustavus | 3-6, 6-4, 10-4 |
| Round of 128 | Jordan SwansonConcordia def. Tyler ZinneckerLUTH | 6-4, 6-2 |
| Round of 128 | Peter DunnCarleton College def. Martin DluhosGrinnell | 6-2, 6-2 |
| Round of 128 | Mitch EslickWartburg def. Samriddh BurmanLuther | 6-1, 6-4 |
| Round of 128 | Chris KunaUW-Eau Claire def. Michael ColemanMacalester | 7-5, 6-0 |
| Round of 128 | Matt WhitesideCarthage def. Jack CullenAugustana | 7-6 (0-4), 3-6, 10-8 |
| Round of 128 | Ryan KingCoe College def. Pawel CzczepkowskiSaint Mary's University | 6-1, 6-1 |
| Round of 128 | Nikko KarnoppGustavus def. Brian TresedderConcordia University | 6-1, 6-1 |
| Round of 128 | Kelvin CaiatiUW-Whitewater def. Brian TollySt. Olaf | 6-3, 6-1 |
| Round of 128 | L Paul VickersUW-La Crosse def. Kevin HilpertSt. Scholastica | 6-1, 6-2 |
| Round of 128 | Sammy RamoniCarthage def. Joel CassensBethel | 6-4, 6-4 |
| Round of 128 | Dmitry GlumovGRINNEL def. Bernard MitamboHamline | 6-1, 7-6 (0-5) |
| Round of 128 | Mike LunkaSaint Mary's University def. Will PalmerAugustana | 6-2, 7-5 |
| Round of 128 | Max PeipkornLuther def. John KeaneLoras College | 6-2, 6-0 |
| Round of 128 | Patrick ClarkGustavus def. Pat SchramkaConcordia University | 6-2, 6-2 |
| Round of 128 | L Caleb RayLawerence def. Brendan AndersonSt. Scholastica | 6-1, 5-7, 13-11 |
| Round of 128 | Timmy MollerUW-Whitewater def. Ali BandealiMacalester | by default |
| Round of 128 | Matt EdinConcordia def. Sam TalarczykUW-L | 6-3, 6-2 |
| Round of 128 | Harry WhiteleyLuther def. Dustin BlackburnUW-Oshkosh | 6-4, 6-3 |
| Round of 128 | Lars OlsonUW-Eau Claire def. Sam TeitelbaumHamline | 6-2, 6-3 |
| Round of 128 | Winston ParkCarleton College def. Nathan FeketeUW-La Crosse | 6-6 (10-0), 6-1 |
| Round of 128 | Curtis NewmanCoe College def. Dutch HansenSaint John's | 7-5, 6-6 (9-0) |
| Round of 128 | Nick GarciaUniv. of Dubuque def. Andre GlassLakeland | 6-1, 6-0 |
| Round of 128 | Derek HarringtonSt. Norbert College def. Joey LaFountaineLuther | 6-3, 6-2 |
| Round of 128 | Knute GundersenSt. Olaf def. Chris VargoCarthage | 2-6, 6-3, 10-7 |
| Round of 128 | Kyle OlsonGustavus def. Max ZlevorLawerence | 6-1, 6-4 |
| Round of 128 | Vic MirasolaUW-La Crosse def. John WightSt. Olaf | 6-0, 6-3 |
| Round of 128 | Greg JanssenCoe College def. Austin JiangCarleton College | 6-1, 6-1 |
| Round of 128 | Titus LevyMacalester def. Cooper SmithLawerence | 6-1, 6-6 (3-0) |
| Round of 128 | Andrew McGlashenLakeland def. Phil LoprinziUW-Eau Claire | 6-7 (0-5), 6-3, 10-8 |
| Round of 128 | Kyle HalwegUW-Whitewater def. Jack SchwaySaint Mary's University | 6-2, 6-4 |
| Round of 128 | Jeffrey LotzCarthage def. Andrew LutzHamline | 6-0, 6-2 |
| Round of 128 | L Mark MeteskiLuther def. Tim DeanSt. Scholastica | 6-2, 6-1 |
| Round of 128 | Amrik DonkenaGustavus def. Chad SmithConcordia | 6-1, 6-0 |
| Round of 128 | Ian HansenSaint John's def. Scottie MartinLuther | 7-5, 6-3 |
| Round of 128 | Adam DeSimoneAugustana def. Cory McCarthyDUB | 6-2, 7-5 |
| Round of 128 | Krishan JethwaGAC def. Ishan BhadkamkarGrinnell | 6-2, 6-2 |
| Round of 128 | Danny GlinertUW-Whitewater def. Alexander ChinCarleton College | 4-6, 6-2, 10-8 |
| Round of 128 | Robbie PriceUW-Oshkosh def. Mike HyrczykSt. Norbert College | 6-3, 6-1 |
| Round of 128 | David CroonquistHamline def. Steven QuiringUW-La Crosse | 2-6, 6-1, 11-9 |
| Round of 128 | Scott StegemannCoe College def. Alex McLeanCarthage | 4-6, 6-1, 10-3 |
| Round of 128 | Bye vs. Scott SundstromLuther | no result |
| Round of 128 | W Jacob EngelstadSt. Scholastica def. Dartanian TaylorLakeland | 6-2, 6-1 |
| Round of 128 | Tom RonningBethel def. Nate KilsdonkUW-Oshkosh | 6-3, 6-2 |
| Round of 128 | JT DelkCARTH def. Kyle HelgemoeHamline | 6-3, 6-3 |
| Round of 128 | Tyler JohnsonGustavus def. Jonathan RogerCoe College | 6-3, 6-1 |
| Round of 128 | Nick PiotrowskiUW-La Crosse def. Paul MairetMacalester | 6-2, 6-0 |
| Round of 128 | Nick MozenaLuther def. Chris MullinAugustana | 6-3, 6-1 |
| Round of 128 | Kirby JohnsonConcordia def. Alec MooreGrinnell | 6-2, 7-6 (0-6) |
| Round of 128 | Ben GuzickCarleton College def. Ustab RijalLuther | 6-2, 7-6 (0-3) |
| Round of 128 | Andy SchwenkeCarthage def. Jason DunnLawerence | 3-6, 6-1, 10-8 |
| Round of 128 | Kevin FawcettUW-Eau Claire def. Victor KhristenkoCoe College | 6-4, 4-6, 10-6 |
| Round of 128 | Jon MahviUW-La Crosse def. Eric KoppmannSt. Norbert College | 6-0, 6-3 |
| Round of 128 | Will VandenbergKenyon def. Aaron GendronLuther | 6-2, 6-1 |
| Round of 128 | Kyle DoyleAugustana def. Eric ScanlanUW-Whitewater | 6-4, 6-1 |
| Round of 128 | Peter WrightGustavus def. Joe HolguinLoras College | 6-3, 4-6, 10-5 |
| Round of 128 | Tom KoenenWartburg def. Steve AnschutzConcordia University | 6-2, 4-6, 10-1 |
| Round of 128 | Bye vs. Juan Carlos PerezGrinnell | no result |
| Round of 64 | Mike GreenbergKenyon def. Nick LehnertAugustana | 6-1, 6-0 |
| Round of 64 | Joey Van LieshoutUW-La Crosse def. Daniel NellisGrinnell | 6-2, 6-3 |
| Round of 64 | Robert BeckerHamline def. Max EdwardsMacalester | 6-3, 6-3 |
| Round of 64 | James LewisonUW-Oshkosh def. Jordan SwansonConcordia | 7-6, 2-1 |
| Round of 64 | Peter DunnCarleton College vs. Mitch EslickWartburg | 1-6, 3-1 |
| Round of 64 | Chris KunaUW-Eau Claire def. Matt WhitesideCarthage | 6-1, 1-0 |
| Round of 64 | Ryan KingCoe College def. Nikko KarnoppGustavus | 6-1, 6-3 |
| Round of 64 | Kelvin CaiatiUW-Whitewater def. Paul VickersUW-La Crosse | 6-2, 6-1 |
| Round of 64 | Sammy RamoniCarthage def. Dmitry GlumovGrinnell | 6-4, 4-6, 6-0 |
| Round of 64 | Mike LunkaSaint Mary's University def. Max PeipkornLuther | 6-4, 3-6, 10-4 |
| Round of 64 | Patrick ClarkGustavus def. Caleb RayLawerence | 6-0, 6-1 |
| Round of 64 | Matt EdinConcordia def. Timmy MollerUW-Whitewater | 4-6, 6-2, 10-6 |
| Round of 64 | Lars OlsonUW-Eau Claire def. Harry WhiteleyLuther | 6-4, 3-6, 10-7 |
| Round of 64 | Winston ParkCarleton College def. Curtis NewmanCoe College | 2-6, 6-2, 10-3 |
| Round of 64 | Nick GarciaUniv. of Dubuque def. Derek HarringtonSt. Norbert College | 6-1, 6-3 |
| Round of 64 | Knute GundersenSt. Olaf def. Kyle OlsonGustavus | 6-3, 6-2 |
| Round of 64 | Greg JanssenCoe College def. John WhiteSt. Olaf | 6-1, 6-2 |
| Round of 64 | Andrew McGlashenLakeland def. Titus LevyMacalester | 7-5, 6-1 |
| Round of 64 | Jeffrey LotzCarthage def. Kyle HalwegUW-Whitewater | 6-2, 6-4 |
| Round of 64 | Amrik DonkenaGustavus def. Mark MeteskiLuther | 4-6, 6-4, 13-11 |
| Round of 64 | Adam DeSimoneAugustana def. Ian HansenSaint John's | 6-4, 6-4 |
| Round of 64 | Danny GlinertUW-Whitewater def. Krishan JethwaGustavus | 6-2, 6-3 |
| Round of 64 | David CroonquistHamline def. Robbie PriceUW-Oshkosh | 6-3, 6-3 |
| Round of 64 | Scott SundstromLuther def. Scott StegemannCoe College | 6-0, 6-1 |
| Round of 64 | L Tom RonningBethel def. Jacob EngelstadSt. Scholastica | 6-2, 6-3 |
| Round of 64 | Tyler JohnsonGustavus def. J.T. DelkCarthage | 6-0, 6-2 |
| Round of 64 | Nick PiotrowskiUW-La Crosse def. Nick MozenaLuther | 6-1, 6-0 |
| Round of 64 | Ben GuzickCarleton College def. Ustab RijalLuther | 6-1, 7-5 |
| Round of 64 | Kevin FawcettUW-Eau Claire def. Andy SchwenkeCarthage | 6-3, 6-2 |
| Round of 64 | Will VandenbergKenyon def. Jon MahviUW-La Crosse | 6-2, 6-2 |
| Round of 64 | Peter WrightGustavus def. Kyle DoyleAugustana | 6-1, 6-2 |
| Round of 64 | Juan Carlos PerezGrinnell def. Tom KoenenWartburg | 6-3, 6-2 |
| Round of 32 | Mike GreenbergKenyon def. Joey Van LieshoutUW-La Crosse | 6-1, 6-0 |
| Round of 32 | James LewisonUW-Oshkosh def. Robert BeckerHamline | 6-0, 6-3 |
| Round of 32 | Peter DunnCarleton College def. Chris KunaUW-Eau Claire | 6-1, 7-5 |
| Round of 32 | Kelvin CaiatiUW-Whitewater def. Ryan KingCoe College | 6-4, 7-5 |
| Round of 32 | Sammy RamoniCarthage def. Mike LunkaSaint Mary's University | 6-1, 6-1 |
| Round of 32 | Matt EdinConcordia def. Patrick ClarkGustavus | 7-5, 4-6, 11-9 |
| Round of 32 | Winston ParkCarleton College def. Lars OlsonUW-Eau Claire | 6-1, 6-3 |
| Round of 32 | Nick GarciaUniv. of Dubuque def. Knute GundersenSt. Olaf | 6-3, 6-3 |
| Round of 32 | Greg JanssenCoe College def. Andrew McGlashenLakeland | 6-4, 6-3 |
| Round of 32 | Amrik DonkenaGustavus def. Jeffrey LotzCarthage | 7-5, 6-1 |
| Round of 32 | Danny GlinertUW-Whitewater def. Adam DeSimoneAugustana | 7-5, 6-3 |
| Round of 32 | Scott SundstromLuther def. David CroonquistHamline | 6-1, 6-0 |
| Round of 32 | Tyler JohnsonGustavus def. Tom RonningBethel | 6-2, 6-7 (0-3), 11-9 |
| Round of 32 | Ben GuzickCarleton College def. Nick PiotrowskiUW-La Crosse | 6-2, 6-3 |
| Round of 32 | Will VandenbergKenyon def. Kevin FawcettUW-Eau Claire | 2-6, 6-2, 10-4 |
| Round of 32 | Juan Carlos PerezGrinnell def. Peter WrightGustavus | 6-3, 6-2 |
| Round of 16 | Mike GreenbergKenyon def. James LewisonUW-Oshkosh | 6-2, 6-1 |
| Round of 16 | Peter DunnCarleton College def. Kelvin CaiatiUW-Whitewater | 7-6 (0-5), 6-4 |
| Round of 16 | Sammy RamoniCarthage def. Matt EdinConcordia | 6-0, 2-6, 6-4 |
| Round of 16 | Nick GarciaUniv. of Dubuque def. Winston ParkCarleton College | 6-7, 6-2, 6-4 |
| Round of 16 | Amrik DonkenaGustavus def. Greg JanssenCoe College | 3-6, 7-6 (0-12), 6-4 |
| Round of 16 | Scott SundstromLuther def. Danny GlinertUW-Whitewater | 6-2, 6-1 |
| Round of 16 | Ben GuzickCarleton College def. Tyler JohnsonGustavus | 6-0, 6-2 |
| Round of 16 | Will VandenbergKenyon def. Juan Carlos PerezGrinnell | 6-2, 6-3 |
| Quarterfinal | Mike GreenbergKenyon def. Peter DunnCarleton College | 6-4, 3-2 |
| Quarterfinal | Sammy RamoniCarthage def. Nick GarciaUniv. of Dubuque | 6-2, 6-3 |
| Quarterfinal | Scott SundstromLuther def. Amrik DonkenaGustavus | 6-1, 6-0 |
| Quarterfinal | Ben GuzickCarleton College def. Will VandenbergKenyon | 6-2, 7-5 |
| Semifinal | Mike GreenbergKenyon def. Sammy RamoniCarthage | 7-6, 4-6, 6-2 |
| Semifinal | Ben GuzickCarleton College def. Scott SundstromLuther | 2-6, 7-5, 6-4 |
| Final | Mike GreenbergKenyon def. Ben GuzickCarleton College | 7-5, 1-6, 6-3 |
