Damien Roberts defeated Louis Vosloo 7-5 3-6 6-1 in the Central Africa Masters 2 qualifying round on hard. The upset overturned the form book — Louis Vosloo came in leading the head-to-head 3–2. Damien Roberts narrowed the head-to-head to 3–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | South Africa Masters 2 | QF | hard | Louis Vosloo | 5-7 6-2 7-5 |
| 1998-11-14 | South Africa 2 Masters 2 | SF | hard | Damien Roberts | 6-2 6-2 |
| 1997-11-22 | South Africa Masters 1 | QF | hard | Louis Vosloo | 6-2 6-2 |
| 1997-10-25 | Central Africa Masters 1 | SF | hard | Louis Vosloo | 7-5 5-7 7-6 |
| 1996-07-28 | Great Britain 3 Masters 4 | R16 | grass | Damien Roberts | 6-2 6-4 |