Federico Dondo defeated Filippo Volandri 6-3 6-2 in the Italy 1 Masters 3 semi-final on clay. The upset overturned the form book — Filippo Volandri came in leading the head-to-head 1–0. Federico Dondo claimed a first win over Filippo Volandri in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-03-15 | Italy F1 | QF | clay | Filippo Volandri | 1-6 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.