Leigh Holland defeated Tim Crichton 6-3 6-4 in the Australia 3 Masters 3 round of 16 on hard. The upset overturned the form book — Tim Crichton came in leading the head-to-head 1–0. Leigh Holland claimed a first win over Tim Crichton in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-11-27 | Australia F4 | R16 | grass | Tim Crichton | 6-3 6-4 |