David Mcnamara defeated Leigh Holland 6-4 6-3 in the Australia F5 round of 16 on grass. The upset overturned the form book — Leigh Holland came in leading the head-to-head 4–0. David Mcnamara claimed a first win over Leigh Holland in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-09-18 | Japan F7 | R32 | hard | Leigh Holland | 6-7(5) 7-5 6-3 |
| 1999-10-25 | Australia F1 | R16 | clay | Leigh Holland | 6-1 6-4 |
| 1999-02-28 | Australia 1 Masters 1 | R32 | clay | Leigh Holland | 6-2 2-6 6-4 |
| 1998-09-19 | Australia 3 Masters 1 | QF | hard | Leigh Holland | 6-3 6-4 |