Anna Kournikova defeated Patty Schnyder 6-0 6-2 in the Amelia Island quarter-final on clay. The result followed the form book — Anna Kournikova came in leading the head-to-head 3–0, defending last year's quarter-final. Anna Kournikova extended the head-to-head to 4–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-24 | Roland Garros | R32 | clay | Anna Kournikova | 6-1 3-6 6-0 |
| 1999-03-29 | Hilton Head | SF | clay | Anna Kournikova | 6-7 6-0 6-3 |
| 1998-04-06 | Amelia Island | R16 | clay | Anna Kournikova | 6-1 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.