Monica Seles defeated Anna Kournikova 6-4 6-3 in the WTA Tour Championships round of 16 on carpet. The result followed the form book — Monica Seles came in leading the head-to-head 4–1, defending last year's round of 16. Monica Seles extended the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-01-29 | Tokyo | SF | hard | Monica Seles | 6-3 3-6 6-3 |
| 2000-07-31 | San Diego | SF | hard | Monica Seles | 6-3 7-6(2) |
| 2000-03-20 | Miami | R16 | hard | Monica Seles | 6-1 3-6 6-0 |
| 1999-02-02 | Tokyo | QF | hard | Monica Seles | 7-5 6-3 |
| 1998-03-19 | Key Biscayne | R32 | hard | Anna Kournikova | 7-5 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.