Lisa Raymond defeated Ai Sugiyama 6-1 6-0 in the Sydney round of 32 on hard. The result followed the form book — Lisa Raymond came in leading the head-to-head 7–6. Lisa Raymond extended the head-to-head to 8–6.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-08-18 | New Haven | R32 | hard | Ai Sugiyama | 3-6 6-2 7-5 |
| 2003-07-28 | San Diego | R32 | hard | Lisa Raymond | 6-0 2-6 6-4 |
| 2002-08-12 | Montreal | R64 | hard | Ai Sugiyama | 6-3 6-1 |
| 2002-07-29 | San Diego | R64 | hard | Ai Sugiyama | 7-5 6-0 |
| 2002-07-22 | Stanford | R32 | hard | Lisa Raymond | 6-4 6-7(3) 6-1 |
| 2002-02-25 | Scottsdale | R32 | hard | Ai Sugiyama | 7-6(3) 6-0 |
| 2002-02-17 | Memphis | SF | hard | Lisa Raymond | 6-2 6-1 |
| 2001-03-21 | Miami | R64 | hard | Lisa Raymond | 6-1 4-0 RET |
| 2001-02-26 | Scottsdale | R16 | hard | Lisa Raymond | 7-5 3-6 6-1 |
| 2000-02-28 | Scottsdale | R32 | hard | Ai Sugiyama | 6-2 6-3 |
| 1999-10-18 | Kremlin Cup | QF | carpet | Lisa Raymond | 6-3 7-5 |
| 1999-03-05 | Indian Wells | R32 | hard | Ai Sugiyama | 7-6 7-5 |
| 1997-11-03 | Chicago | R16 | carpet | Lisa Raymond | 6-4 6-2 |
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 172). ATP, WTA & Challenger.