Andrew Gregory defeated Jarryd Maher 6-4 6-1 in the Australia F8 round of 16 on hard. The upset overturned the form book — Jarryd Maher came in leading the head-to-head 1–0. Andrew Gregory claimed a first win over Jarryd Maher in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-08-10 | Germany F14 | R16 | clay | Jarryd Maher | 6-2 2-6 7-5 |