Christian Hill defeated Courage Anyidoho 6-4 6-3 in the West Africa Masters 2 semi-final on hard. The upset overturned the form book — Courage Anyidoho came in leading the head-to-head 1–0. Christian Hill claimed a first win over Courage Anyidoho in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-08 | West Africa Masters 1 | R32 | hard | Courage Anyidoho | 6-2 4-6 7-5 |