Leigh Holland defeated Jaymon Crabb 6-4 6-2 in the Australia 1 Masters 3 round of 16 on clay. Leigh Holland extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-11-25 | Australia F4 | R32 | grass | Leigh Holland | 3-6 6-4 6-2 |
| 1997-11-02 | Australia 4 Masters 3 | R16 | hard | Jaymon Crabb | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.