Leigh Holland defeated Owen Casey 7-6 6-4 in the Indonesia Masters 4 qualifying round on hard. The upset overturned the form book — Owen Casey came in leading the head-to-head 2–1. Leigh Holland narrowed the head-to-head to 2–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-06-05 | Ireland F2 | R16 | carpet | Owen Casey | 6-2 1-6 7-6(1) |
| 1995-08-19 | Indonesia Masters 3 | SF | hard | Owen Casey | 7-5 6-3 |
| 1995-07-23 | Malaysia 2 Masters 2 | R16 | hard | Leigh Holland | 7-6 0-6 7-6 |