Miles Armstrong defeated Kaden Hensel 7-6 6-4 in the Australia F7 qualifying round on clay. Miles Armstrong extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-12-01 | Australia F12 | R16 | hard | Kaden Hensel | 6-3 3-6 6-1 |
| 2008-11-24 | Australia F11 | R16 | hard | Miles Armstrong | 5-7 6-3 6-4 |