Xin Yuan Yu defeated Tobias Clemens 7-6 7-5 in the China F1 round of 16 on hard. The upset overturned the form book — Tobias Clemens came in leading the head-to-head 1–0. Xin Yuan Yu claimed a first win over Tobias Clemens in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-01-12 | China F2 | R32 | hard | Tobias Clemens | 7-6(3) 6-2 |