Miles Armstrong defeated Joshua Crowe 6-3 4-6 6-4 in the Australia F10 round of 32 on hard. The upset overturned the form book — Joshua Crowe came in leading the head-to-head 1–0. Miles Armstrong claimed a first win over Joshua Crowe in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-04 | Australia F4 | R32 | clay | Joshua Crowe | 7-5 7-6(6) |