| UTR Pro Urayasu | 2024/05/09 04:30 | Taiki Hosokawa v Toa Maeda | 5-7,2-6 |
| UTR Pro Urayasu | 2024/05/10 00:00 | Haruki Katsushima v Masaya Kobayashi | 6-2,5-3 |
| UTR Pro Urayasu | 2024/05/09 06:00 | Nicholas Jovanovski v Masaya Kobayashi | 3-6,7-6,6-3 |
| UTR Pro Urayasu | 2024/05/06 00:00 | Koki Takada v Masaya Kobayashi | 6-2,6-2 |
| UTR Pro Kawaguchi | 2024/03/09 02:15 | Masaya Kobayashi v Yuki Karatsu | 2-6,3-6 |
| UTR Pro Kawaguchi | 2024/03/08 03:30 | Masaya Kobayashi v Haruki Katsushima | 2-6,1-6 |
| UTR Pro Kawaguchi | 2024/03/07 01:00 | Masaya Kobayashi v Yuto Miyagawa | 6-2,6-4 |
| UTR Pro Kawaguchi | 2024/03/04 23:30 | Masaya Kobayashi v Hiiro Sakamoto | 5-7,5-7 |
| ITF M15 Karuizawa | 2019/05/27 00:00 | Masaya Kobayashi v Jake Delaney | 0-6,5-7 |