Serena Williams defeated Monica Seles 6-2 6-3 in the Key Biscayne round of 16 on hard. The result followed the form book — Serena Williams came in leading the head-to-head 3–1, defending last year's quarter-final. Serena Williams extended the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-08-13 | Toronto | SF | hard | Serena Williams | 7-5 7-6(5) |
| 2001-08-06 | Los Angeles | QF | hard | Monica Seles | 6-2 3-6 7-6(2) |
| 1999-08-30 | US Open | QF | hard | Serena Williams | 4-6 6-3 6-2 |
| 1997-11-03 | Chicago | QF | carpet | Serena Williams | 4-6 6-1 6-1 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. Small sample — read as indicative. About
Averages over each player's completed matches in the selected window (199 vs 1). ATP, WTA & Challenger.