Matwe Middelkoop advanced when Motaz Abou El Khair retired 6-1 2-0 in the Rwanda F1 semi-final. Matwe Middelkoop extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2007-11-19 | Uganda F1 | QF | clay | Matwe Middelkoop | 6-4 6-2 |
| 2003-09-22 | Rwanda F1 | R16 | clay | Matwe Middelkoop | 6-1 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.