Nathan Healey defeated David To 6-4 6-2 in the Australia F2 qualifying round on grass. The result followed the form book — Nathan Healey came in leading the head-to-head 1–0. Nathan Healey extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-02-25 | New Zealand F1 | R32 | hard | Nathan Healey | 6-7(1) 6-3 7-6(0) |