Gwinyai Tongoona defeated Oliver Freelove 3-6 6-3 6-3 in the South and Central Africa 4 round of 16 on hard. The upset overturned the form book — Oliver Freelove came in leading the head-to-head 1–0, but Gwinyai Tongoona had been the form player, winning 2 of their last 6 on hard. Gwinyai Tongoona claimed a first win over Oliver Freelove in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-11-10 | South and Central Africa 1 | R32 | hard | Oliver Freelove | 6-2 4-6 6-4 |