Alexandros Jakupovic defeated Claudio Grassi 1-6 7-6 6-1 in the Ireland F1 round of 32 on carpet. The upset overturned the form book — Claudio Grassi came in leading the head-to-head 2–1. Alexandros Jakupovic narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-08-19 | Switzerland F5 | QF | clay | Claudio Grassi | 6-2 6-4 |
| 2011-07-18 | Turkey F20 | QF | clay | Alexandros Jakupovic | 6-2 6-2 |
| 2010-10-04 | Italy F29 | QF | hard | Claudio Grassi | 6-1 3-6 7-6(5) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.