Andrej Kracman defeated Pieter Calitz 6-4 6-7 6-1 in the South Africa Masters 2 round of 16 on hard. The upset overturned the form book — Pieter Calitz came in leading the head-to-head 1–0. Andrej Kracman claimed a first win over Pieter Calitz in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | South Africa Masters 1 | SF | hard | Pieter Calitz | 6-2 6-3 |