Leigh Holland defeated Chris Rae 6-3 5-7 6-2 in the Australia 1 Masters 4 round of 32 on hard. The result followed the form book — Leigh Holland came in leading the head-to-head 2–0. Leigh Holland extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-19 | Australia 3 Masters 3 | QF | hard | Leigh Holland | 6-4 5-7 6-4 |
| 1999-09-19 | Australia 3 Masters 4 | R16 | hard | Leigh Holland | 6-2 5-7 6-3 |