Antonio Pastorino defeated Rui Machado 2-6 7-5 6-3 in the Italy F27 round of 32 on clay. The upset overturned the form book — Rui Machado came in leading the head-to-head 1–0. Antonio Pastorino claimed a first win over Rui Machado in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-12 | Italy F13 | F | clay | Rui Machado | 6-4 3-6 7-6(1) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.