John James defeated Grant Doyle 6-4 7-5 in the Australia 1 Masters 3 round of 32 on clay. The upset overturned the form book — Grant Doyle came in leading the head-to-head 1–0. John James claimed a first win over Grant Doyle in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-19 | Australia 3 Masters 4 | R16 | hard | Grant Doyle | 6-0 6-4 |