Damien Roberts defeated Charlie Singer 6-3 6-7 6-2 in the Central Africa Masters 2 qualifying round on hard. The upset overturned the form book — Charlie Singer came in leading the head-to-head 1–0. Damien Roberts claimed a first win over Charlie Singer in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-07-28 | Great Britain 3 Masters 1 | QF | grass | Charlie Singer | 6-4 6-4 |