Jennifer Capriati defeated Ai Sugiyama 7-5 7-6 in the WTA Tour Championships round robin on carpet. The result followed the form book — Jennifer Capriati came in leading the head-to-head 4–3, defending last year's semi-final. Jennifer Capriati extended the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-08-30 | US Open | R16 | hard | Jennifer Capriati | 7-5 6-2 |
| 2002-08-12 | Montreal | R16 | hard | Jennifer Capriati | 6-1 7-5 |
| 2002-08-04 | Los Angeles | QF | hard | Ai Sugiyama | 6-3 6-3 |
| 2000-01-17 | Australian Open | QF | hard | Jennifer Capriati | 6-0 6-2 |
| 1998-08-03 | San Diego | R32 | hard | Ai Sugiyama | 5-7 6-2 6-2 |
| 1997-11-10 | Philadelphia | R32 | carpet | Ai Sugiyama | 6-1 6-2 |
| 1997-03-31 | Hilton Head | R32 | clay | Jennifer Capriati | 6-1 6-0 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.