Kaden Hensel defeated Andrew Gregory 7-6 6-4 in the Australia F8 round of 32 on hard. The upset overturned the form book — Andrew Gregory came in leading the head-to-head 1–0, but Kaden Hensel had been the form player, winning 2 of their last 7 on hard. Kaden Hensel 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 | R32 | hard | Andrew Gregory | 5-7 3-0 |