Justin Bower defeated Louis Vosloo 6-0 6-2 in the USA F12 qualifying round on clay. Justin Bower extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | South Africa Masters 2 | F | hard | Justin Bower | 7-5 7-6 |
| 1999-10-16 | South Africa Masters 4 | SF | hard | Louis Vosloo | 2-6 7-6 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.