Maxime Boye defeated Filippo Volandri 4-6 6-1 6-3 in the Italy F4 round of 32 on clay. The upset overturned the form book — Filippo Volandri came in leading the head-to-head 1–0. Maxime Boye claimed a first win over Filippo Volandri in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-21 | Italy 3 Masters 2 | F | clay | Filippo Volandri | 6-2 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.