Bobbie Altelaar defeated Colin Bennett 6-4 1-6 6-2 in the Portugal 5 Masters 4 qualifying round on clay. The upset overturned the form book — Colin Bennett came in leading the head-to-head 1–0. Bobbie Altelaar claimed a first win over Colin Bennett in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-11-22 | Portugal 5 Masters 2 | R16 | clay | Colin Bennett | 7-6 7-5 |