Angeles Montolio defeated Justine Henin 5-7 7-6 6-4 in the Estoril semi-final on clay. The result followed the form book — Angeles Montolio came in defending last year's quarter-final. Angeles Montolio extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-03 | Athens 25K | SF | clay | Angeles Montolio | 6-4 6-0 |
| 1999-03-15 | Reims 25K | SF | clay | Justine Henin | 6-2 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.