Alina Jidkova defeated Jolene Watanabe 6-3 4-6 7-6 in the Mahwah 50K qualifying round on hard. The upset overturned the form book — Jolene Watanabe came in leading the head-to-head 2–1, but Alina Jidkova had been the form player, winning 4 of their last 9 on hard. Alina Jidkova narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-04 | Albuquerque 50K | R32 | hard | Jolene Watanabe | 7-5 6-4 |
| 1999-03-22 | Atlanta 25K | R16 | hard | Jolene Watanabe | 6-2 6-2 |
| 1999-01-25 | Clearwater 25K | SF | hard | Alina Jidkova | 7-6 4-6 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.