Nathan Healey defeated David To 6-7 6-3 7-6 in the New Zealand F1 round of 32 on hard. 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 |
|---|---|---|---|---|---|
| 2008-02-11 | Australia F2 | QF | grass | Nathan Healey | 6-4 6-2 |