Andrew Gregory advanced when Kaden Hensel retired 5-7 3-0 in the Australia F8 round of 32. Andrew Gregory claimed a first win over Kaden Hensel in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-10-06 | Australia F8 | R32 | hard | Kaden Hensel | 7-6(5) 6-4 |