Alexandros Jakupovic defeated Tom Kocevar Desman 7-6 3-6 7-6 in the Greece F5 qualifying round on hard. The upset overturned the form book — Tom Kocevar Desman 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 |
|---|---|---|---|---|---|
| 2014-10-13 | Greece F8 | R32 | hard | Tom Kocevar Desman | 7-5 6-0 |
| 2013-10-28 | Greece F17 | R32 | hard | Tom Kocevar Desman | 6-3 6-1 |
| 2010-10-25 | Greece F3 | SF | carpet | Alexandros Jakupovic | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.