Leigh Holland defeated Andrew Painter 6-3 6-3 in the New Zealand Masters 3 round of 32 on hard. The upset overturned the form book — Andrew Painter came in leading the head-to-head 1–0, but Leigh Holland had been the form player, winning 2 of their last 4 on hard. Leigh Holland claimed a first win over Andrew Painter in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-09-22 | Australia 2 Masters 3 | R16 | hard | Andrew Painter | 6-4 6-3 |