Leigh Holland defeated Heath Denman 7-5 7-5 in the Australia 1 Masters 1 round of 16 on clay. The result followed the form book — Leigh Holland came in leading the head-to-head 1–0. Leigh Holland extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-19 | Australia 3 Masters 2 | R32 | hard | Leigh Holland | 6-2 6-1 |