Jamie Holmes defeated Jaymon Crabb 2-6 6-2 6-1 in the Australia 4 Masters 4 round of 16 on hard. The upset overturned the form book — Jaymon Crabb came in leading the head-to-head 1–0. Jamie Holmes claimed a first win over Jaymon Crabb in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-10-27 | Australia 3 Masters 3 | QF | clay | Jaymon Crabb | 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.