Glenn Knox defeated Jaymon Crabb 6-3 6-4 in the Australia 3 Masters 3 qualifying round on hard. The upset overturned the form book — Jaymon Crabb came in leading the head-to-head 4–0. Glenn Knox claimed a first win over Jaymon Crabb in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-10-02 | Australia 3 Masters 2 | R32 | hard | Jaymon Crabb | 6-1 6-2 |
| 1999-09-19 | Australia 3 Masters 4 | R32 | hard | Jaymon Crabb | 6-2 6-3 |
| 1998-10-28 | Australia F1 | R16 | clay | Jaymon Crabb | 6-1 6-3 |
| 1998-05-10 | Australia 2 Masters 4 | R16 | hard | Jaymon Crabb | 7-5 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.