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