Chen Astrogo defeated Mika Urbancic 7-5 6-4 in the Karshi 25K round of 32 on hard. The upset overturned the form book — Mika Urbancic came in leading the head-to-head 2–0. Chen Astrogo claimed a first win over Mika Urbancic in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-03-24 | Athens-Goudi 10K | R16 | hard | Mika Urbancic | 6-2 7-5 |
| 2007-11-19 | Ramat Hasharon 10K | R32 | hard | Mika Urbancic | 7-6(3) 0-6 6-4 |