Lisa Raymond defeated Conchita Martinez 2-6 6-3 6-2 in the Wimbledon round of 32 on grass. The upset overturned the form book — Conchita Martinez came in leading the head-to-head 6–3, defending last year's quarter-final. Lisa Raymond narrowed the head-to-head to 6–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-06-14 | Eastbourne | R32 | grass | Conchita Martinez | 3-6 6-2 6-0 |
| 2004-03-10 | Indian Wells | R32 | hard | Conchita Martinez | 6-4 7-5 |
| 2002-09-10 | Waikoloa | QF | hard | Lisa Raymond | 6-4 6-7(2) 6-4 |
| 1999-06-21 | Wimbledon | R32 | grass | Lisa Raymond | 6-3 6-1 |
| 1998-10-05 | Filderstadt | R16 | hard | Lisa Raymond | 6-4 2-6 6-2 |
| 1998-08-31 | US Open | R32 | hard | Conchita Martinez | 6-3 3-6 6-2 |
| 1998-07-25 | Fed Cup WG1 SF: ESP vs USA | RR | clay | Conchita Martinez | 7-6(1) 6-4 |
| 1998-04-06 | Amelia Island | QF | clay | Conchita Martinez | 6-4 7-5 |
| 1997-07-28 | San Diego | R32 | hard | Conchita Martinez | 6-3 3-6 6-1 |
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About
Averages over each player's completed matches in the selected window (46 vs 18). ATP, WTA & Challenger.