Damien Roberts defeated Justin Bower 6-4 7-6 in the South Africa Masters 1 round of 32 on hard. The upset overturned the form book — Justin Bower came in leading the head-to-head 2–1. Damien Roberts 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 2 | SF | hard | Justin Bower | 6-4 6-2 |
| 1997-11-22 | South Africa Masters 3 | QF | hard | Justin Bower | 7-6 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.