Luke Milligan defeated Oliver Freelove 7-6 6-3 in the Great Britain F4 round of 32 on clay. The result followed the form book — Luke Milligan came in leading the head-to-head 2–1. Luke Milligan extended the head-to-head to 3–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-09-23 | Great Britain F8 | R16 | hard | Luke Milligan | 6-4 6-2 |
| 2000-08-14 | Great Britain F7 | R32 | hard | Oliver Freelove | 4-5(5) 5-3 4-0 2-4 5-4(5) |
| 1998-07-26 | Great Britain Masters 4 | R16 | grass | Luke Milligan | 6-3 6-7 6-2 |