Nathan Healey defeated Raphael Durek 7-6 6-3 in the New Zealand F2 qualifying round on hard. The result followed the form book — Nathan Healey came in leading the head-to-head 2–1. Nathan Healey extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-02-11 | Australia F2 | F | grass | Raphael Durek | 6-3 6-2 |
| 2004-03-08 | Australia F1 | R16 | hard | Nathan Healey | 6-2 6-2 |
| 2003-06-16 | Nottingham | Q32 | grass | Nathan Healey | 6-0 3-6 6-4 |