Owen Casey defeated Scott Barron 6-4 6-3 in the Caribbean 1 Masters 1 round of 16 on hard. The upset overturned the form book — Scott Barron came in leading the head-to-head 1–0. Owen Casey claimed a first win over Scott Barron in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-29 | Ireland F1 | R16 | carpet | Scott Barron | 6-1 6-4 |