Jaymon Crabb defeated Leigh Holland 6-2 6-1 in the Australia 4 Masters 3 round of 16 on hard. The upset overturned the form book — Leigh Holland came in leading the head-to-head 2–0, but Jaymon Crabb had been the form player, winning 3 of their last 4 on hard. Jaymon Crabb claimed a first win over Leigh Holland in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-28 | Australia 1 Masters 3 | R16 | clay | Leigh Holland | 6-4 6-2 |
| 1998-11-25 | Australia F4 | R32 | grass | Leigh Holland | 3-6 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.