Jennifer Capriati defeated Chanda Rubin 6-3 4-6 6-3 in the Sydney round of 32 on hard. The upset overturned the form book — Chanda Rubin came in leading the head-to-head 4–3, but Jennifer Capriati had been the form player, winning 6 of their last 8 on hard. Jennifer Capriati narrowed the head-to-head to 4–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-06-16 | Eastbourne | SF | grass | Chanda Rubin | 2-6 7-6(5) 6-2 |
| 2003-03-19 | Miami | SF | hard | Jennifer Capriati | 6-2 6-4 |
| 2000-10-28 | Quebec City | F | hard | Chanda Rubin | 6-4 6-2 |
| 2000-10-02 | Filderstadt | R32 | hard | Chanda Rubin | 6-0 6-7(11) 6-2 |
| 2000-03-20 | Miami | R32 | hard | Jennifer Capriati | 6-1 6-3 |
| 1999-11-01 | Quebec City | F | hard | Jennifer Capriati | 4-6 6-1 6-2 |
| 1997-05-05 | Rome | R64 | clay | Chanda Rubin | 7-6 6-2 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (31 vs 22). ATP, WTA & Challenger.