Jan Ralph Brandt defeated Luke Milligan 6-4 6-2 in the Greece F2 semi-final 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 |
| 1998-09-30 | Great Britain F8 | QF | hard | Jan Ralph Brandt | 6-4 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.