Leonardo Azzaro defeated Massimo Dellacqua 4-6 6-3 6-4 in the Italy F8 round of 32 on clay. The upset overturned the form book — Massimo Dellacqua came in leading the head-to-head 2–0. Leonardo Azzaro claimed a first win over Massimo Dellacqua in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 1 | R16 | clay | Massimo Dellacqua | 6-4 6-1 |
| 1998-05-18 | Italy F6 | QF | clay | Massimo Dellacqua | 7-6 7-6 |
Averages over each player's completed matches in the selected window (4 vs 6). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About