David Critchley defeated David Kepka 6-4 6-4 in the Canada F3 round of 32 on hard. The result followed the form book — David Critchley came in leading the head-to-head 1–0. David Critchley extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-28 | Canada F3 | R32 | hard | David Critchley | 6-3 7-6 |