Jocelyn Robichaud defeated Louis Vosloo 6-4 2-6 6-3 in the USA 1 Masters 2 round of 64 on hard. The upset overturned the form book — Louis Vosloo came in leading the head-to-head 2–1. Jocelyn Robichaud narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-14 | Canada F1 | QF | hard | Louis Vosloo | 6-2 7-6 |
| 1998-06-15 | Canada F1 | SF | hard | Jocelyn Robichaud | 6-0 7-6 |
| 1997-04-04 | USA 1 Masters 4 | R32 | hard | Louis Vosloo | 6-7 6-3 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.