Justin Bower defeated Damien Roberts 7-6 6-1 in the South Africa Masters 3 qualifying round on hard. The upset overturned the form book — Damien Roberts came in leading the head-to-head 2–1, but Justin Bower had been the form player, winning 7 of their last 8 on hard. Justin Bower narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-10-17 | Central Africa Masters 1 | SF | hard | Damien Roberts | 3-6 7-5 7-6 |
| 1997-11-22 | South Africa Masters 1 | R32 | hard | Damien Roberts | 6-4 7-6 |
| 1997-11-22 | South Africa Masters 2 | SF | hard | Justin Bower | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.