Tim Crichton defeated Leigh Holland 6-3 6-4 in the Australia F4 round of 16 on grass. The upset overturned the form book — Leigh Holland came in leading the head-to-head 1–0. Tim Crichton claimed a first win over Leigh Holland in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-19 | Australia 3 Masters 3 | R16 | hard | Leigh Holland | 6-3 6-4 |