Charles Edouard Maria defeated Gianluca Bolognino 6-4 4-6 7-6 in the Italy 5 2 round of 16 on clay. The upset overturned the form book — Gianluca Bolognino came in leading the head-to-head 1–0, but Charles Edouard Maria had been the form player, winning 3 of their last 7 on clay. Charles Edouard Maria claimed a first win over Gianluca Bolognino in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Italy F15 | R32 | clay | Gianluca Bolognino | 1-0 |