Venus Williams defeated Steffi Graf 6-2 6-4 in the Key Biscayne semi-final on hard. The upset overturned the form book — Steffi Graf came in leading the head-to-head 2–1. Venus Williams narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-21 | Wimbledon | QF | grass | Steffi Graf | 6-2 3-6 6-4 |
| 1999-02-15 | Hanover | SF | carpet | Venus Williams | 6-3 3-6 6-3 |
| 1999-01-11 | Sydney | QF | hard | Steffi Graf | 4-6 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.