Silvia Farina Elia defeated Anna Kournikova 7-6 4-6 6-1 in the Kremlin Cup round of 32 on carpet. The upset overturned the form book — Anna Kournikova came in leading the head-to-head 4–1. Silvia Farina Elia narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-30 | Leipzig | R16 | carpet | Anna Kournikova | 6-3 6-1 |
| 1999-03-05 | Indian Wells | R64 | hard | Silvia Farina Elia | 7-6 1-6 7-5 |
| 1999-01-11 | Sydney | R32 | hard | Anna Kournikova | 4-6 6-3 7-5 |
| 1998-08-31 | US Open | R32 | hard | Anna Kournikova | 6-4 6-1 |
| 1998-02-18 | Hanover | R32 | carpet | Anna Kournikova | 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.