Bertrand Madsen defeated Peter Clarke 7-6 6-3 in the Australia 1 Masters 1 qualifying round on hard. The result followed the form book — Bertrand Madsen came in leading the head-to-head 2–1. Bertrand Madsen extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-28 | Australia 1 Masters 3 | R32 | clay | Bertrand Madsen | 6-4 6-4 |
| 1999-02-28 | Australia 1 Masters 4 | SF | clay | Peter Clarke | 3-6 6-4 6-4 |
| 1998-03-01 | Australia 1 Masters 2 | SF | hard | Bertrand Madsen | 6-4 7-5 |