Riccardo Ciruolo defeated Leonardo Azzaro 7-5 6-1 in the Italy F15 round of 32 on clay. The upset overturned the form book — Leonardo Azzaro came in leading the head-to-head 2–1. Riccardo Ciruolo narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-19 | Italy 2 Masters 4 | F | clay | Riccardo Ciruolo | 6-1 6-4 |
| 1998-11-07 | Egypt 2 Masters 1 | R32 | hard | Leonardo Azzaro | 7-6 6-2 |
| 1998-11-07 | Egypt 2 Masters 3 | R16 | hard | Leonardo Azzaro | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.