-- 1998-99 Men's Tennis -- Season Record: 14-9 /// Northwest Conference Record 11-1 Unless otherwise noted, all home matches played in the Bratton Tennis Center, Whitman College, Walla Walla, Wash.
+ Northwest Conference opponent
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| Date | Time | Opponent/Event | Location | Results |
| Sat, Oct 2 - Mon, Oct 4 | All Day | Pacific Northwest Small College Championships | Walla Walla WA | Details |
| Sat, Oct 9 - Tue, Oct 12 | All Day | ITA West Region Division III Tournament | Claremont CA | Details |
| Fri, Feb 4 | 8 pm | * University of Montana | Home | L, 7-0 |
| Sat, Feb 5 | 10 am | * University of Portland | Home | L, 7-0 |
| Sun, Feb 6 | 6 pm | *** UC-Santa Cruz | Home | L, 7-0 |
| Sat, Feb 19 | 2 pm | + Whitworth College | Home | W, 7-0 |
| Sun, Feb 20 | 1 pm | ** Montana State-Billings | Home | W, 7-0 |
| Tue, Feb 22 | 5 pm | % Albertson College | Home | Cancelled |
| Sat, Feb 26 | 2 pm | + Seattle University | Home | W, 7-0 |
| Sun, Feb 27 | 1 pm | + Pacific Lutheran University | Home | W, 5-2 |
| Mon, Feb 28 | 10 am | + University of Puget Sound | Home | W, 6-1 |
| Sat, Mar 4 | 2:30 pm | University of Calgary | Home | W, 5-2 |
| Mon, Mar 6 | 9 am | + Lewis & Clark College | Portland OR | W, 7-0 |
| Mon, Mar 6 | 2 pm | + Pacific University | Forest Grove OR | W, 7-0 |
| Wed, Mar 15 | 9 am | % Dominican College | Home | L, 7-0 |
| Wed, Mar 15 | 2 pm | % Albertson College | Home | W, 5-2 |
| Mon, Mar 20 | TBA | *** University of Redlands | Redlands CA | Rain delay; Match to resume March 23 |
| Tue, Mar 21 | 1 pm | *** Claremont-Mudd-Scripps Colleges | Claremont CA | L, 7-0 |
| Thu, Mar 23 | 2:30 pm | *** University of Redlands | Redlands CA | L, 7-0 |
| Fri, Mar 24 | 2 pm | *** Pomona-Pitzer Colleges | Claremont CA | L, 5-2 |
| Sat, Mar 25 | 2 pm | *** UC-San Diego | San Diego CA | Canceled by rain |
| Mon, Apr 10 | 3:30 pm | + Pacific Lutheran University | Tacoma WA | W, 4-3 |
| Tue, Apr 11 | 10 am | + University of Puget Sound | Tacoma WA | W, 6-1 |
| Tue, Apr 11 | 2 pm | + Seattle University | Tacoma WA | W, 7-0 |
| Fri, Apr 14 | 3:30 pm | + Whitworth College | Spokane WA | W, 7-0 |
| Mon, Apr 17 | 10 am | + Linfield College | Home | W, 6-1 |
| Mon, Apr 17 | 2 pm | + Willamette University | Home | L, 7-0 |
| Tue, Apr 18 | Noon | % Lewis-Clark State College | Home | L, 6-1 |
| Sun, Apr 23 | 2:30 pm | Northwest Conference Championships: Whitman vs. George Fox |
Tualatin Hills Recreation Center, Tualatin OR |
W, 6-1 |
| Mon, Apr 24 | 9:30 am | Northwest Conference Championships: Whitman vs. Pacific Lutheran |
Tualatin Hills Recreation Center, Tualatin OR |
L, 4-3 |
| Mon, Apr 24 | 2:30 pm | Northwest Conference Championships: Whitman vs. Puget Sound |
Tualatin Hills Recreation Center, Tualatin OR |
L, 5-1 |