John James defeated Jaymon Crabb 7-5 6-0 in the Australia 1 Masters 1 round of 32 on clay. The upset overturned the form book — Jaymon Crabb came in leading the head-to-head 1–0. John James claimed a first win over Jaymon Crabb in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-19 | Australia 3 Masters 2 | R32 | hard | Jaymon Crabb | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.