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January 22, 1999 at University of Toledo (at Laurel Hills)
| Event | Kalamazoo College | U of Toledo | Winner | Score |
| 1 Singles | Kyle Harding | Gernot Kerschbaumer | Toledo | 6-4, 6-3 |
| 2 Singles | Andrew Minnelli | Jorge Morales | Toledo | 6-2, 6-4 |
| 3 Singles | Ryan Shockley | Anthony Lipp | Kalamazoo | 6-3, 7-5 |
| 4 Singles | Toby Ernst | Nebojsa Stojanovich | Kalamazoo | 7-6, 6-2 |
| 5 Singles | Bob Pennington | Hector Arroyo | Toledo | 4-6, 6-3, 6-3 |
| 6 Singles | Jeremy Cox | Josh Weinstein | Kalamazoo | 7-5, 6-2 |
| 1 Doubles | Toby Ernst
Kyle Harding |
Jorge Morales
Hector Arroyo |
Toledo | 9-8 |
| 2 Doubles | Andrew Minnelli
Ryan Shockley |
Gernot Kerschbaumer
Nebojsa Stojanovich |
Toledo | 8-6 |
| 3 Doubles | Jeremy Cox
Bob Pennington |
Anthony Lipp
Josh Weinstein |
Toledo | 8-2 |
| Match Score: | Toledo 4-3 |
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