Arantxa Sanchez Vicario defeated Serena Williams 6-2 6-1 in the Sydney semi-final on hard. The result followed the form book — Arantxa Sanchez Vicario came in defending last year's round of 16. Arantxa Sanchez Vicario extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-08-14 | Montreal | SF | hard | Serena Williams | 6-2 6-4 |
| 1999-09-27 | Grand Slam Cup | QF | hard | Serena Williams | 6-3 6-1 |
| 1999-08-09 | Manhattan Beach | QF | hard | Serena Williams | 6-2 6-3 |
| 1999-05-10 | Berlin | QF | grass | Arantxa Sanchez Vicario | 6-3 3-2 RET |
| 1998-06-15 | Eastbourne | QF | grass | Arantxa Sanchez Vicario | 4-6 6-4 6-4 |
| 1998-05-25 | Roland Garros | R16 | clay | Arantxa Sanchez Vicario | 4-6 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.