Julia Vakulenko defeated Valentina Sassi 6-2 6-4 in the Wimbledon q64 on grass. The upset overturned the form book — Valentina Sassi came in leading the head-to-head 2–0. Julia Vakulenko claimed a first win over Valentina Sassi in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-21 | Maribor 25K | R16 | clay | Valentina Sassi | 6-4 6-2 |
| 1999-11-27 | Mallorca 10K | R16 | clay | Valentina Sassi | 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.