Oliver Freelove defeated David Sherwood 6-3 7-5 in the Great Britain F7 round of 32 on hard. The result followed the form book — Oliver Freelove came in leading the head-to-head 1–0. Oliver Freelove extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1998-07-26 | Great Britain Masters 4 | R32 | grass | Oliver Freelove | 6-7 6-2 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.