Grant Doyle defeated Ben Mathias 7-5 6-0 in the Australia 3 Masters 2 round of 16 on hard. 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 |
|---|---|---|---|---|---|
| 1999-11-22 | Australia F4 | R32 | grass | Grant Doyle | 6-7 7-5 6-1 |