Anna Kournikova defeated Andrea Glass 4-6 6-2 6-3 in the Australian Open round of 32 on hard. The result followed the form book — Anna Kournikova came in leading the head-to-head 1–0, defending last year's round of 32. Anna Kournikova extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-29 | Hilton Head | QF | clay | Anna Kournikova | 6-2 2-1 RET |