Stefano Ianni defeated Philip Bester 7-6 6-3 in the USA F11 semi-final on clay. The upset overturned the form book — Philip Bester came in leading the head-to-head 1–0. Stefano Ianni claimed a first win over Philip Bester in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-11 | USA F11 | QF | clay | Philip Bester | 7-6(4) 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.