Leonardo Azzaro defeated Nahuel Fracassi 6-7 6-4 6-2 in the Slovenia F1 round of 16 on clay. The result followed the form book — Leonardo Azzaro came in leading the head-to-head 2–1. Leonardo Azzaro extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 3 | R16 | clay | Nahuel Fracassi | 6-3 3-6 6-4 |
| 1999-06-19 | Italy 2 Masters 4 | R32 | clay | Leonardo Azzaro | 7-6 6-4 |
| 1997-08-02 | Italy 5 Masters 4 | R32 | clay | Leonardo Azzaro | 6-2 4-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.