Ross Matheson defeated Miles Maclagan 6-3 7-5 in the Turkey Masters 3 qualifying round on hard. The upset overturned the form book — Miles Maclagan came in leading the head-to-head 2–0. Ross Matheson claimed a first win over Miles Maclagan in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1995-04-24 | Great Britain 2 Masters 4 | QF | clay | Miles Maclagan | 7-6 6-2 |
| 1993-09-12 | Great Britain 3 Masters 2 | R32 | hard | Miles Maclagan | 7-5 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.