Patrik Fredriksson defeated Luke Milligan 5-7 6-4 6-4 in the Great Britain F5 round of 32 on clay. The upset overturned the form book — Luke Milligan came in leading the head-to-head 1–0. Patrik Fredriksson claimed a first win over Luke Milligan in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-05-05 | Great Britain F6 | F | clay | Luke Milligan | 6-4 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.