Jennifer Capriati defeated Nathalie Tauziat 1-6 6-4 6-2 in the Canadian Open round of 32 on hard. The result followed the form book — Jennifer Capriati came in leading the head-to-head 2–1. Jennifer Capriati extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-08 | Philadelphia | R16 | carpet | Nathalie Tauziat | 6-4 3-6 7-5 |
| 1999-08-30 | US Open | R32 | hard | Jennifer Capriati | 6-3 1-6 6-1 |
| 1999-05-17 | Strasbourg | QF | clay | Jennifer Capriati | 6-1 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.