Martin Blackman defeated Sean Cole 6-2 7-5 in the Caribbean 1 Masters 1 qualifying round on clay. The upset overturned the form book — Sean Cole came in leading the head-to-head 1–0. Martin Blackman claimed a first win over Sean Cole in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1991-03-30 | Caribbean 1 Masters 4 | R16 | clay | Sean Cole | 4-6 7-5 7-5 |