| 10/2 | 2009 Midwest ITA Tennis Tournament | Round of 64 | Brendan Anderson | L 2-8 | Jeffrey Lotz / Sammy Ramoni |
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| 2/6 | University of St. Thomas | No. 2 | Brendan Anderson | L 4-8 | Brendan O'Connell / Kevin Walker |
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| 2/7 | at Hamline University | No. 2 | Brendan Anderson | L 6-8 | Bernard Mitambo / Sam Teitelbaum |
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| 2/20 | Saint John's University | No. 2 | Jacob Engelstad | L 5-8 | Fabricio Moncada / Dutch Hansen |
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| 2/27 | at St. Cloud State | No. 1 | Jacob Engelstad | L 8-9 (6-8) | Shane Ecklund / Aaron Johnson |
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| 3/15 | vs. Saint Ambrose | No. 2 | Jacob Engelstad | W 8-6 | Michael Harts / Ryan Vretis |
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| 3/15 | vs. Augustana College (S.D.) | No. 1 | Jacob Engelstad | L 4-8 | Jared Drenkow / Evan Gardner |
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| 3/16 | vs. UW-La Crosse | No. 2 | Jacob Engelstad | L 5-8 | Nathan Fekete / Steven Quiring |
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| 3/18 | vs. Springfield | No. 2 | Jacob Engelstad | W 8-3 | Benjamin Burnap / Zach O'Leary |
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| 3/19 | vs. Franklin & Marshall | No. 2 | Jacob Engelstad | W 8-3 | Paul Salierno / Josh Calo |
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| 3/26 | at Northwestern | No. 2 | Jacob Engelstad | W 8-2 | Joshua Fread / Caleb Kauss |
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| 3/27 | at Bethany Lutheran | No. 1 | Jacob Engelstad | W 8-0 | David Blumer / Paul Webber |
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| 3/27 | vs. North Central University | No. 1 | Jacob Engelstad | W 8-0 | Josiah Tonder / Corey Kalinowski |
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| 4/10 | at Martin Luther | No. 2 | Jacob Engelstad | W 8-4 | David Zuberbier / Andrew Becker |
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| 4/11 | vs. Luther College | No. 2 | Jacob Engelstad | L 7-9 | Max Piepkorn / Scott Martin |
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| 4/16 | North Central University | No. 1 | Jacob Engelstad | W 8-0 | Josiah Tonder / Corey Kalinowski |
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| 4/17 | Northwestern | No. 2 | Jacob Engelstad | W 9-7 | Joshua Fread / Keagen Blancke |
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| 4/17 | Martin Luther | No. 2 | Jacob Engelstad | W 8-0 | David Zuberbier / Andrew Becker |
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| 4/18 | Minnesota-Morris | No. 2 | Jacob Engelstad | W 8-0 | Caleb Power / Nathan West |
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| 4/25 | at UW-Eau Claire | No. 2 | Jacob Engelstad | L 4-8 | Chris Kuna / Dirk Van Rybroek |
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| 5/7–8 | 2010 UMAC Men's Tennis Tournament | Semifinal | Jacob Engelstad | W 8-2 | Chris Droske / Caleb Power |
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| 5/7–8 | 2010 UMAC Men's Tennis Tournament | Consolation | Jacob Engelstad | W 8-3 | Keagen Blancke / Joshua Fread |
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