Lisa Raymond defeated Monica Seles 6-4 6-2 in the Stanford quarter-final on hard. The upset overturned the form book — Monica Seles came in leading the head-to-head 2–1, defending last year's semi-final. Lisa Raymond narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-03-20 | Miami | R32 | hard | Monica Seles | 6-3 6-2 |
| 1998-04-06 | Amelia Island | R16 | clay | Lisa Raymond | 7-6 6-4 |
| 1992-08-31 | US Open | R64 | hard | Monica Seles | 7-5 6-0 |
Averages over each player's completed matches in the selected window (46 vs 1). ATP, WTA & Challenger.
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