Leonardo Azzaro defeated Carlo Santoro 6-2 3-6 6-0 in the Italy 2 Masters 4 round of 32 on clay. The upset overturned the form book — Carlo Santoro came in leading the head-to-head 1–0. Leonardo Azzaro claimed a first win over Carlo Santoro in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-10-04 | Italy 6 Masters 2 | R16 | clay | Carlo Santoro | 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.