Sergio Gaoni defeated Chris Rae 6-1 7-5 in the Australia 3 Masters 1 round of 32 on hard. The upset overturned the form book — Chris Rae came in leading the head-to-head 1–0, but Sergio Gaoni had been the form player, winning 2 of their last 5 on hard. Sergio Gaoni claimed a first win over Chris Rae in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-07-19 | USA F11 | R64 | hard | Chris Rae | 6-3 6-2 |