Oliver Freelove defeated Gwinyai Tongoona 6-2 4-6 6-4 in the South and Central Africa 1 round of 32 on hard. The upset overturned the form book — Gwinyai Tongoona came in leading the head-to-head 1–0. Oliver Freelove claimed a first win over Gwinyai Tongoona in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-11-10 | South and Central Africa 4 | R16 | hard | Gwinyai Tongoona | 3-6 6-3 6-3 |