Andrew Painter defeated Tate Roberts 7-5 6-4 in the New Zealand Masters 2 round of 32 on hard. The result followed the form book — Andrew Painter came in leading the head-to-head 1–0. Andrew Painter extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-09-19 | Australia 3 Masters 2 | R32 | hard | Andrew Painter | 6-4 6-7 7-6 |