Andrew Rueb defeated Damien Roberts 6-2 7-6 in the South Africa Masters 1 round of 32 on hard. The upset overturned the form book — Damien Roberts came in leading the head-to-head 1–0. Andrew Rueb claimed a first win over Damien Roberts in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-10-26 | Central Africa Masters 4 | R16 | hard | Damien Roberts | 7-5 6-3 |