James Davidson defeated Graeme Darlington 7-5 6-1 in the Great Britain Masters 2 round of 32 on grass. The upset overturned the form book — Graeme Darlington came in leading the head-to-head 1–0. James Davidson claimed a first win over Graeme Darlington in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-09-30 | Great Britain F8 | R32 | hard | Graeme Darlington | 6-3 7-6 |