Nicholas Chisholm defeated Donavan September 4-6 7-6 6-4 in the South Africa Masters 1 round of 32 on hard. The result followed the form book — Nicholas Chisholm came in leading the head-to-head 2–0. Nicholas Chisholm extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-18 | Central Africa Masters 1 | QF | hard | Nicholas Chisholm | 6-4 5-7 6-4 |
| 1999-09-18 | Central Africa Masters 2 | SF | hard | Nicholas Chisholm | 3-6 6-2 6-4 |