David Sherwood defeated Luke Milligan 6-1 6-4 in the Great Britain F8 semi-final on hard. The upset overturned the form book — Luke Milligan came in leading the head-to-head 2–0. David Sherwood claimed a first win over Luke Milligan in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-27 | Great Britain F9 | R32 | hard | Luke Milligan | 6-4 6-2 |
| 1998-07-26 | Great Britain Masters 3 | R16 | grass | Luke Milligan | 6-3 1-6 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.