Leonardo Azzaro defeated Marco Monnecchi 3-6 6-4 7-6 in the Italy 2 Masters 1 round of 32 on clay. Leonardo Azzaro extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-06-16 | Italy F10 | QF | clay | Leonardo Azzaro | 6-2 4-6 6-3 |
| 1997-06-28 | Italy 4 Masters 4 | R32 | clay | Marco Monnecchi | 7-5 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.