Kaden Hensel defeated Miles Armstrong 6-3 3-6 6-1 in the Australia F12 round of 16 on hard. The upset overturned the form book — Miles Armstrong came in leading the head-to-head 2–0. Kaden Hensel claimed a first win over Miles Armstrong in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-11-24 | Australia F11 | R16 | hard | Miles Armstrong | 5-7 6-3 6-4 |
| 2007-10-08 | Australia F7 | QF | clay | Miles Armstrong | 7-6(8) 6-4 |