Massimo Dellacqua defeated Filip Prpic 6-0 6-3 in the Italy F25 qualifying round on hard. The upset overturned the form book — Filip Prpic came in leading the head-to-head 1–0, but Massimo Dellacqua had been the form player, winning 2 of their last 4 on hard. Massimo Dellacqua claimed a first win over Filip Prpic in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-09-14 | Italy F28 | QF | hard | Filip Prpic | 1-6 6-4 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.