Dejan Petrovic advanced when Grant Silcock retired 4-2 in the Australia F2 round of 32. Dejan Petrovic extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | Australia F3 | QF | grass | Dejan Petrovic | 7-6 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.