Grant Silcock defeated Jamie Holmes 6-3 4-6 7-6 in the Australia 2 Masters 1 round of 16 on hard. The upset overturned the form book — Jamie Holmes came in leading the head-to-head 1–0, but Grant Silcock had been the form player, winning 2 of their last 5 on hard. Grant Silcock claimed a first win over Jamie Holmes in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-09-22 | Australia 2 Masters 4 | R32 | hard | Jamie Holmes | 6-4 6-1 |