Daniele Giorgini advanced when Leonardo Azzaro retired 3-6 4-1 in the Italy F4 round of 32. Daniele Giorgini narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-03-03 | Italy F3B | SF | clay | Leonardo Azzaro | 6-3 6-0 |
| 2006-10-02 | Italy F34 | F | clay | Leonardo Azzaro | 6-2 5-7 6-4 |
| 2006-02-13 | Italy F1 | F | clay | Daniele Giorgini | 6-4 3-6 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.