Anna Kournikova defeated Conchita Martinez 6-3 6-0 in the Key Biscayne round of 16 on hard. The upset overturned the form book — Conchita Martinez came in leading the head-to-head 5–2. Anna Kournikova narrowed the head-to-head to 5–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-04-07 | Charleston | R64 | clay | Conchita Martinez | 6-4 1-1 RET |
| 2002-07-29 | San Diego | R16 | hard | Anna Kournikova | 1-6 6-2 6-1 |
| 2002-04-15 | Charleston | R64 | clay | Conchita Martinez | 7-6(5) 6-1 |
| 2000-11-13 | WTA Tour Championships | QF | carpet | Anna Kournikova | 6-4 6-0 |
| 1998-08-17 | Canadian Open | R16 | hard | Conchita Martinez | 6-0 6-3 |
| 1998-05-11 | Berlin | SF | grass | Conchita Martinez | 6-0 6-1 |
| 1998-03-05 | Indian Wells | R16 | hard | Conchita Martinez | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.