Ryan Henry defeated Andrew Derer 7-6 6-4 in the Australia 2 3 round of 32 on hard. The upset overturned the form book — Andrew Derer came in leading the head-to-head 2–0. Ryan Henry claimed a first win over Andrew Derer in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-09-20 | Australia 2 Satellite 4 | QF | hard | Andrew Derer | 6-1 6-2 |
| 2002-01-28 | Australia 1 4 | R32 | hard | Andrew Derer | 6-7(3) 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.