Vincenzo Santopadre defeated Davide Sanguinetti 7-6 6-2 in the San Marino round of 16 on clay. The upset overturned the form book — Davide Sanguinetti came in leading the head-to-head 2–1, defending last year's round of 16. Vincenzo Santopadre narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-01-17 | Australian Open | Q32 | hard | Davide Sanguinetti | 6-3 6-4 |
| 1999-05-10 | Rome Masters | R64 | clay | Davide Sanguinetti | 1-6 6-2 6-3 |
| 1992-07-06 | Italy 2 Masters 3 | R16 | clay | Vincenzo Santopadre | 6-3 6-4 |
Averages over each player's completed matches in the selected window (40 vs 200). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About