Gianluca Luddi defeated Massimo Dellacqua 6-3 3-6 6-4 in the Italy F3 round of 16 on clay. The upset overturned the form book — Massimo Dellacqua came in leading the head-to-head 1–0. Gianluca Luddi claimed a first win over Massimo Dellacqua in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-02 | Italy F15 | R16 | clay | Massimo Dellacqua | 6-3 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.