Jan Ralph Brandt defeated Luke Milligan 6-4 6-3 in the Great Britain F8 qualifying round on hard. Jan Ralph Brandt extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-29 | Ireland F1 | R16 | carpet | Luke Milligan | 6-3 6-2 |
| 1999-05-17 | Greece F2 | SF | hard | Jan Ralph Brandt | 6-4 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.