Andrew Painter defeated Jamie Holmes 4-6 6-4 6-3 in the Australia 2 Masters 2 round of 32 on hard. The upset overturned the form book — Jamie Holmes came in leading the head-to-head 1–0. Andrew Painter claimed a first win over Jamie Holmes in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-10-08 | Australia 2 Masters 4 | R32 | hard | Jamie Holmes | 6-4 6-2 |