Tomoe Hotta defeated Kirstin Freye 6-3 6-4 in the Saga 25K round of 32 on grass. The upset overturned the form book — Kirstin Freye came in leading the head-to-head 1–0. Tomoe Hotta claimed a first win over Kirstin Freye in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-05 | Edmonton 25K | R32 | hard | Kirstin Freye | 3-6 6-1 6-3 |