James Auckland defeated Simon Dickson 1-6 6-4 7-5 in the Great Britain F1 round of 32 on carpet. The upset overturned the form book — Simon Dickson came in leading the head-to-head 2–0. James Auckland claimed a first win over Simon Dickson in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-04-23 | China F2 | R16 | hard | Simon Dickson | 6-3 6-0 |
| 1999-09-20 | Great Britain F8 | R32 | hard | Simon Dickson | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.