Leigh Holland defeated Heath Denman 6-2 6-1 in the Australia 3 Masters 2 round of 32 on hard. 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 |
|---|---|---|---|---|---|
| 1999-02-28 | Australia 1 Masters 1 | R16 | clay | Leigh Holland | 7-5 7-5 |