Josh Tuckfield defeated Leigh Holland 6-4 7-6 in the Australia 1 Masters 4 round of 16 on hard. The upset overturned the form book — Leigh Holland came in leading the head-to-head 1–0. Josh Tuckfield claimed a first win over Leigh Holland in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-05-10 | Australia 2 Masters 2 | R32 | hard | Leigh Holland | 6-3 6-2 |