Stadium: Grandstand Court Round: 26 Ground: Hardcourt indoor
| ITF M15 Heraklion | 2019/11/27 11:30 | Boris Pokotilov v Tobias Simon | 6-4,6-4 |
| ITF M15 Sarreguemines | 2019/11/24 14:00 | Tobias Simon v Antoine Bellier | 4-6,6-7 |
| ITF M15 Sarreguemines | 2019/11/23 15:40 | Hugo Schott v Tobias Simon | 6-7,6-7 |
| ITF M15 Sarreguemines | 2019/11/22 15:35 | Tobias Simon v Jonathan Mridha | 6-7,6-4,6-4 |
| ITF M15 Sarreguemines | 2019/11/21 13:35 | Tobias Simon v Justin Eleveld | 7-6,6-4 |
| ITF M15 Sarreguemines | 2019/11/19 17:05 | Tobias Simon v Batiste Klein | 7-5,7-5 |
| Challenger Pune | 2019/11/11 10:30 | Tobias Simon v Aryan Goveas | 4-6,6-7 |
| Challenger Eckental | 2019/10/29 11:40 | Botic Van De Zandschulp v Tobias Simon | 6-4,6-7,7-6 |
| Challenger Pune | 2019/11/13 09:30 | Steven Diez v Yusuke Takahashi | 6-2,6-2 |
| Challenger Pune | 2019/11/11 08:55 | Siddharth Vishwakarma v Yusuke Takahashi | 0-6,6-3,3-6 |
| Challenger Kobe | 2019/11/04 04:00 | Yunseong Chung v Yusuke Takahashi | 7-6,7-6 |
| Challenger Liuzhou | 2019/10/21 04:45 | Danylo Kalenichenko v Yusuke Takahashi | 6-2,6-2 |
| ITF M25 Tay Ninh | 2019/10/04 08:00 | Yusuke Takahashi v Kazuki Nishiwaki | 0-6,6-3,2-6 |
| ITF M25 Tay Ninh | 2019/10/03 02:00 | Yusuke Takahashi v Naoki Nakagawa | 6-4,6-3 |
| ITF M25 Tay Ninh | 2019/10/01 03:30 | Yusuke Takahashi v Linh Giang Trinh | 6-1,6-4 |
| Challenger Kaohsiung | 2019/09/17 03:45 | Harry Bourchier v Yusuke Takahashi | 3-6,6-1,6-2 |