Grant Doyle defeated Ben Mathias 6-7 7-5 6-1 in the Australia F4 round of 32 on grass. The result followed the form book — Grant Doyle came in leading the head-to-head 1–0. Grant Doyle extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-19 | Australia 3 Masters 2 | R16 | hard | Grant Doyle | 7-5 6-0 |