Dejan Petrovic defeated Jay Gooding 6-4 6-2 in the Australia F1 round of 16 on hard. Dejan Petrovic extended the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-22 | Australia F4 | R32 | grass | Dejan Petrovic | 7-6 6-2 |
| 1999-02-28 | Australia 1 Masters 1 | QF | clay | Jay Gooding | 6-3 2-6 6-4 |
| 1999-02-28 | Australia 1 Masters 4 | R32 | clay | Dejan Petrovic | 6-0 6-2 |
| 1996-09-22 | Australia 2 Masters 4 | R32 | hard | Jay Gooding | 7-6 3-6 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.