Andrej Kracman defeated Justin Bower 5-7 7-5 7-5 in the South Africa Masters 1 round of 16 on hard. The upset overturned the form book — Justin Bower came in leading the head-to-head 1–0. Andrej Kracman claimed a first win over Justin Bower in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-16 | South Africa Masters 2 | SF | hard | Justin Bower | 7-5 7-6 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.