Carlo Santoro defeated Massimo Valeri 6-2 4-6 6-2 in the Italy 3 Masters 3 round of 32 on clay. The upset overturned the form book — Massimo Valeri came in leading the head-to-head 1–0, but Carlo Santoro had been the form player, winning 6 of their last 10 on clay. Carlo Santoro claimed a first win over Massimo Valeri in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-05-31 | Italy 3 Masters 1 | QF | clay | Massimo Valeri | 6-2 3-6 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.