Sergio Gaoni defeated Lee Pearson 6-4 6-2 in the Australia 3 Masters 1 round of 32 on hard. The upset overturned the form book — Lee Pearson came in leading the head-to-head 1–0. Sergio Gaoni claimed a first win over Lee Pearson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-04-14 | New Zealand F2 | R32 | hard | Lee Pearson | 6-7 6-1 6-2 |