Glenn Knox defeated Peter Clarke 2-6 7-5 6-4 in the Australia F3 qualifying round on grass. The upset overturned the form book — Peter Clarke came in leading the head-to-head 5–0. Glenn Knox claimed a first win over Peter Clarke in six meetings, narrowing the head-to-head to 5–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-08 | Australia 2 Masters 2 | QF | hard | Peter Clarke | 6-3 6-4 |
| 1999-04-21 | New Zealand F3 | R16 | hard | Peter Clarke | 6-3 6-4 |
| 1999-04-14 | New Zealand F2 | R32 | hard | Peter Clarke | 6-4 6-3 |
| 1999-02-28 | Australia 1 Masters 1 | R16 | clay | Peter Clarke | 6-3 6-3 |
| 1998-09-19 | Australia 3 Masters 3 | R16 | hard | Peter Clarke | 6-3 6-3 |