Colin Bennett defeated Bobbie Altelaar 7-6 7-5 in the Portugal 5 Masters 2 round of 16 on clay. The upset overturned the form book — Bobbie Altelaar came in leading the head-to-head 1–0. Colin Bennett claimed a first win over Bobbie Altelaar in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1997-11-22 | Portugal 5 Masters 4 | QF | clay | Bobbie Altelaar | 6-4 1-6 6-2 |