Andrew Painter defeated Leigh Holland 6-4 6-3 in the Australia 2 Masters 3 round of 16 on hard. The upset overturned the form book — Leigh Holland came in leading the head-to-head 1–0. Andrew Painter claimed a first win over Leigh Holland in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-04-07 | New Zealand Masters 3 | R32 | hard | Leigh Holland | 6-3 6-3 |