Masahide Sakamoto advanced when Kotaro Miyachi retired 3-6 6-2 2-0 in the Japan F6 round of 16. Masahide Sakamoto claimed a first win over Kotaro Miyachi in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-06-07 | Japan 1 Masters 4 | R32 | hard | Kotaro Miyachi | 6-3 7-5 |