Jaymon Crabb defeated John James 6-2 6-1 in the Australia 3 Masters 2 round of 32 on hard. The upset overturned the form book — John James came in leading the head-to-head 1–0. Jaymon Crabb claimed a first win over John James in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-02-28 | Australia 1 Masters 1 | R32 | clay | John James | 7-5 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.