Alan Mackin defeated Oliver Freelove 6-4 4-6 6-4 in the Great Britain F7 round of 16 on hard. The result followed the form book — Alan Mackin came in leading the head-to-head 1–0. Alan Mackin extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-09-20 | Great Britain F8 | QF | hard | Alan Mackin | 6-3 2-6 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.