Leigh Holland defeated Nathan Healey 7-5 6-3 in the Australia 4 Masters 1 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 |
|---|---|---|---|---|---|
| 1999-09-19 | Australia 3 Masters 3 | R32 | hard | Leigh Holland | 5-7 6-4 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.