Louis Vosloo defeated Pieter Calitz 6-4 6-7 6-4 in the South Africa F2 round of 32 on hard. Louis Vosloo extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | South Africa Masters 1 | QF | hard | Pieter Calitz | 6-2 4-6 7-5 |
| 1999-10-16 | South Africa Masters 3 | SF | hard | Louis Vosloo | 6-0 6-4 |