Grant Doyle defeated Heath Denman 7-5 1-6 6-1 in the Australia 2 Masters 2 semi-final on hard. Grant Doyle extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-19 | Australia 3 Masters 1 | R16 | hard | Heath Denman | 6-3 3-6 6-3 |
| 1996-03-03 | Australia 1 Masters 1 | SF | clay | Grant Doyle | 4-6 6-4 6-1 |
| 1995-10-08 | Australia 2 Masters 1 | R32 | hard | Grant Doyle | – |
| 1995-10-08 | Australia 2 Masters 2 | R16 | hard | Heath Denman | 6-2 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.