Rodrigo Monte defeated Leonardo Azzaro 7-6 7-6 in the Italy 2 Masters 2 round of 16 on clay. Rodrigo Monte extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-04-29 | Portugal 1 4 | F | clay | Rodrigo Monte | 7-5 6-3 |
| 1999-11-29 | Chile F6 | R16 | clay | Leonardo Azzaro | 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.