Grant Doyle defeated John James 6-0 6-4 in the Australia 3 Masters 4 round of 16 on hard. The upset overturned the form book — John James came in leading the head-to-head 1–0. Grant Doyle 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 3 | R32 | clay | John James | 6-4 7-5 |