Gero Kretschmer defeated Jan Masik 6-4 7-6 in the United Arab Emirates F2 qualifying round on hard. The upset overturned the form book — Jan Masik came in leading the head-to-head 1–0. Gero Kretschmer claimed a first win over Jan Masik in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-19 | Czech Rep F3 | R16 | clay | Jan Masik | 4-6 6-3 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.