Graeme Darlington defeated Justin Layne 6-3 7-6 in the Great Britain F7 round of 32 on hard. The upset overturned the form book — Justin Layne came in leading the head-to-head 1–0. Graeme Darlington claimed a first win over Justin Layne in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-22 | Bangladesh F1 | R32 | hard | Justin Layne | 2-6 6-4 7-5 |