Luke Milligan defeated Simon Dickson 2-6 7-6 7-6 in the Great Britain F7 round of 32 on hard. The result followed the form book — Luke Milligan came in leading the head-to-head 1–0. Luke Milligan extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-11 | Great Britain F11 | R16 | hard | Luke Milligan | 6-2 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.