Marco Monnecchi defeated Massimo Dellacqua 6-1 6-7 6-1 in the Italy 2 Masters 4 round of 32 on clay. The upset overturned the form book — Massimo Dellacqua came in leading the head-to-head 1–0. Marco Monnecchi 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 | R32 | clay | Massimo Dellacqua | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.