Damien Roberts defeated Shaun Rudman 6-1 7-5 in the Central Africa Masters 1 round of 16 on hard. The result followed the form book — Damien Roberts came in leading the head-to-head 1–0. Damien Roberts extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | South Africa Masters 1 | R16 | hard | Damien Roberts | 6-3 6-3 |