Jamie Holmes defeated Grant Doyle 6-4 6-2 in the Australia 2 Masters 3 qualifying round on hard. The upset overturned the form book — Grant Doyle came in leading the head-to-head 6–0. Jamie Holmes claimed a first win over Grant Doyle in seven meetings, narrowing the head-to-head to 6–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-09-22 | Australia 2 Masters 3 | SF | hard | Grant Doyle | 6-2 6-3 |
| 1994-09-25 | Australia 2 Masters 1 | SF | hard | Grant Doyle | 2-6 7-6 6-4 |
| 1994-09-25 | Australia 2 Masters 4 | R16 | hard | Grant Doyle | 6-2 4-6 6-3 |
| 1993-02-26 | Australia 1 Masters 2 | R16 | carpet | Grant Doyle | 7-5 6-2 |
| 1992-03-02 | Australia 1 Masters 2 | QF | carpet | Grant Doyle | 5-7 6-2 6-1 |
| 1992-03-02 | Australia 1 Masters 4 | F | carpet | Grant Doyle | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.