Filippo Volandri defeated Federico Dondo 1-6 6-2 6-1 in the Italy F1 qualifying round on clay. The upset overturned the form book — Federico Dondo came in leading the head-to-head 1–0. Filippo Volandri claimed a first win over Federico Dondo in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-13 | Italy 1 Masters 3 | SF | clay | Federico Dondo | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.