Jarryd Maher defeated Andrew Gregory 6-2 2-6 7-5 in the Germany F14 round of 16 on clay. The upset overturned the form book — Andrew Gregory came in leading the head-to-head 1–0. Jarryd Maher claimed a first win over Andrew Gregory in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-10-12 | Australia F8 | R16 | hard | Andrew Gregory | 6-4 6-1 |