Kris Van Wyk advanced when Khololwam Montsi retired 6-1 in the M15 Hillcrest 2 semi-final. Kris Van Wyk narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2026-07-03 | M15 Hillcrest | QF | hard | Khololwam Montsi | 6-1 6-4 |
| 2024-06-27 | M25 Hillcrest 1 | R16 | hard | Khololwam Montsi | 6-2 6-0 |
| 2022-10-07 | M15 Maputo 1 | QF | hard | Kris Van Wyk | 2-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.