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