Masashi Tokumaru defeated Alex Sugai 6-0 6-2 in the Japan 2 Masters 2 round of 32 on hard. The result followed the form book — Masashi Tokumaru came in leading the head-to-head 1–0. Masashi Tokumaru extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-10-18 | Japan F5 | R32 | carpet | Masashi Tokumaru | 4-6 7-5 6-2 |