Chris Rae defeated Glenn Knox 5-7 6-3 7-5 in the Australia 3 Masters 1 round of 32 on hard. The upset overturned the form book — Glenn Knox came in leading the head-to-head 3–0. Chris Rae claimed a first win over Glenn Knox in four meetings, narrowing the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-02-21 | Australia 1 Masters 1 | R32 | hard | Glenn Knox | 4-6 6-3 7-6(6) |
| 1999-11-22 | Australia F4 | R32 | grass | Glenn Knox | 6-4 6-3 |
| 1998-11-18 | Australia F3 | R32 | grass | Glenn Knox | 6-2 6-1 |