Gianluca Gatto defeated Leonardo Azzaro 7-6 6-0 in the Italy 5 Masters 1 round of 32 on clay. The upset overturned the form book — Leonardo Azzaro came in leading the head-to-head 3–0. Gianluca Gatto claimed a first win over Leonardo Azzaro in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-01-23 | Central America Masters 3 | R32 | clay | Leonardo Azzaro | 4-6 6-3 6-3 |
| 1998-06-16 | Italy F10 | R32 | clay | Leonardo Azzaro | 6-4 5-7 7-6 |
| 1997-06-28 | Italy 4 Masters 2 | R16 | clay | Leonardo Azzaro | 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.