Jeroen Masson defeated Nick Mcdonald 6-4 6-4 in the South Africa 2 Masters 3 round of 32 on hard. The upset overturned the form book — Nick Mcdonald came in leading the head-to-head 1–0, but Jeroen Masson had been the form player, winning 2 of their last 4 on hard. Jeroen Masson claimed a first win over Nick Mcdonald in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | South Africa Masters 2 | R32 | hard | Nick Mcdonald | 3-6 7-6 6-2 |