Shaun Rudman defeated Jeroen Masson 4-6 6-4 6-1 in the South Africa 2 Masters 1 round of 32 on hard. The upset overturned the form book — Jeroen Masson came in leading the head-to-head 1–0. Shaun Rudman claimed a first win over Jeroen Masson in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-05 | Mauritius South Africa 1 | R16 | hard | Jeroen Masson | 6-1 6-4 |