Alexandros Jakupovic defeated Theodoros Angelinos 6-3 6-3 in the Portugal F3 round of 32 on hard. The upset overturned the form book — Theodoros Angelinos came in leading the head-to-head 3–2, but Alexandros Jakupovic had been the form player, winning 5 of their last 9 on hard. Alexandros Jakupovic narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-10-07 | Greece F14 | QF | hard | Theodoros Angelinos | 6-3 6-2 |
| 2013-05-06 | Greece F6 | QF | hard | Alexandros Jakupovic | 3-6 6-2 6-1 |
| 2009-09-21 | Greece F1 | SF | hard | Theodoros Angelinos | 6-7(9) 7-6(6) 7-6(5) |
| 2009-05-11 | Romania F2 | R32 | clay | Theodoros Angelinos | 6-3 3-6 6-4 |
| 2003-08-11 | Romania F8 | R32 | clay | Alexandros Jakupovic | 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.