Benjamin Cassaigne defeated Damien Roberts 6-4 6-7 6-1 in the South Africa Masters 1 qualifying round on hard. The upset overturned the form book — Damien Roberts came in leading the head-to-head 1–0. Benjamin Cassaigne claimed a first win over Damien Roberts in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | South Africa Masters 3 | R16 | hard | Damien Roberts | 6-4 6-1 |