Massimo Valeri defeated Carlo Santoro 6-2 3-6 6-1 in the Italy 3 Masters 1 qualifying round on clay. The upset overturned the form book — Carlo Santoro came in leading the head-to-head 1–0. Massimo Valeri claimed a first win over Carlo Santoro in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-05-31 | Italy 3 Masters 3 | R32 | clay | Carlo Santoro | 6-2 4-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.