Gwinyai Tongoona defeated Andrew Anderson 3-6 7-5 6-2 in the Botswana F1 round of 16 on hard. The upset overturned the form book — Andrew Anderson came in leading the head-to-head 4–0. Gwinyai Tongoona claimed a first win over Andrew Anderson in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-09-05 | Kenya F1 | QF | hard | Andrew Anderson | 6-2 6-0 |
| 2004-09-27 | Rwanda F1 | R16 | clay | Andrew Anderson | 6-3 6-0 |
| 2001-05-28 | South Africa F1 | R32 | hard | Andrew Anderson | 6-4 6-4 |
| 2000-10-16 | South Africa 2 | R16 | hard | Andrew Anderson | 6-1 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.