Claudio Grassi defeated Alexandros Jakupovic 6-1 3-6 7-6 in the Italy F29 qualifying round on hard. The upset overturned the form book — Alexandros Jakupovic came in leading the head-to-head 2–1. Claudio Grassi 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 |
| 2006-06-19 | Ireland F1 | R32 | carpet | Alexandros Jakupovic | 1-6 7-6(2) 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.