Chris Rae defeated Sergio Gaoni 6-3 6-2 in the USA F11 round of 64 on hard. The upset overturned the form book — Sergio Gaoni came in leading the head-to-head 1–0. Chris Rae claimed a first win over Sergio Gaoni in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-19 | Australia 3 Masters 1 | R32 | hard | Sergio Gaoni | 6-1 7-5 |