Round: 62 Ground: Hardcourt outdoor
| Others | 2016/11/12 06:10 | Yong-Kyu Lim v Masaya Kobayashi | 6-2,6-3 |
| Others | 2016/11/12 00:30 | Masaya Kobayashi v Ryota Tanuma | 6-3,6-3 |
| Others | 2016/11/05 06:55 | Masaya Kobayashi v Sergey Betov | 2-6,1-6 |
| ITF Japan F7 Qual | 2016/06/05 01:00 | Masaya Kobayashi v Chan-Yeong Oh | 2-6,6-3,3-6 |
| ITF Japan F7 Qual | 2016/06/04 01:00 | Masaya Kobayashi v Daisuke Sumizawa | 6-2,7-6 |
| ITF Japan F6 | 2016/05/31 04:00 | Duckhee Lee v Masaya Kobayashi | 6-1,6-1 |
| ITF Japan F4 | 2016/03/29 03:00 | Makoto Ochi v Masaya Kobayashi | 6-3,6-1 |
| ITF Japan F2 | 2016/03/19 03:50 | Masaya Kobayashi v Soonwoo Kwon | 6-7,0-6 |
| ITF Japan F8 | 2016/06/16 02:15 | Keisuke Watanuki v Sho Katayama | 3-6,1-6 |
| ITF Japan F8 | 2016/06/15 04:30 | Shunrou Takeshima v Keisuke Watanuki | 6-7,0-6 |
| ITF Japan F7 | 2016/06/09 02:30 | Chan-Yeong Oh v Keisuke Watanuki | 6-3,6-7,6-4 |
| ITF Japan F7 | 2016/06/07 01:00 | Keisuke Watanuki v Takuto Niki | 6-4,7-6 |
| ITF Japan F6 | 2016/05/31 05:25 | Yusuke Takahashi v Keisuke Watanuki | 6-3,6-4 |
| ITF Japan F6 Qual | 2016/05/29 04:00 | Keisuke Watanuki v Sho Shimabukuro | 6-1,6-0 |
| ITF Japan F6 Qual | 2016/05/28 01:00 | Keisuke Watanuki v Shin Yoshida | 6-1,6-4 |
| ITF Japan F5 | 2016/04/06 03:40 | Keisuke Watanuki v Sho Katayama | 2-6,5-7 |