James Fox defeated Barry Cowan 3-6 6-1 6-2 in the Great Britain 3 Masters 1 round of 32 on grass. The upset overturned the form book — Barry Cowan came in leading the head-to-head 4–1. James Fox narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1996-07-28 | Great Britain 3 Masters 2 | R32 | grass | James Fox | 5-7 6-4 6-4 |
| 1994-08-28 | Great Britain 3 Masters 2 | R32 | grass | Barry Cowan | 6-1 4-6 6-3 |
| 1994-04-18 | Great Britain 2 Masters 4 | R32 | hard | Barry Cowan | 6-1 6-7 6-3 |
| 1993-11-27 | Pakistan Masters 3 | QF | hard | Barry Cowan | 6-2 6-2 |
| 1993-10-30 | Thailand Bangladesh Masters 4 | R16 | hard | Barry Cowan | 6-4 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.