Yasufumi Yamamoto defeated Masahide Sakamoto 6-4 6-1 in the Canada F3 round of 32 on hard. The result followed the form book — Yasufumi Yamamoto came in leading the head-to-head 1–0. Yasufumi Yamamoto extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-07 | Japan 1 Masters 3 | R16 | hard | Yasufumi Yamamoto | 6-3 6-4 |