James Sekulov advanced when Jamie Holmes retired 6-2 in the Australia 2 Masters 2 round of 16. James Sekulov narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-10-27 | Australia 3 Masters 2 | QF | clay | Jamie Holmes | 6-3 3-6 7-5 |
| 1996-09-22 | Australia 2 Masters 2 | QF | hard | James Sekulov | 6-2 1-6 7-6 |
| 1994-02-27 | Australia 1 Masters 2 | R16 | carpet | Jamie Holmes | 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.