Stadium: Center Court Round: 166 Ground: Hardcourt outdoor
| Challenger Shanghai | 2019/09/11 04:15 | Kaichi Uchida v Yusuke Takahashi | 4-6,7-6,6-0 |
| Challenger Shanghai | 2019/09/10 02:30 | Chuhan Wang v Yusuke Takahashi | 4-6,4-6 |
| ITF M15 Hua Hin | 2019/09/07 03:00 | Makoto Ochi v Yusuke Takahashi | 6-2,4-6,6-1 |
| ITF M15 Hua Hin | 2019/09/06 03:00 | Takashi Saito v Yusuke Takahashi | 2-6,2-6 |
| ITF M15 Hua Hin | 2019/09/05 03:00 | Bradley Mousley v Yusuke Takahashi | 2-6,7-6,3-6 |
| ITF M15 Hua Hin | 2019/09/04 03:00 | Tsung-Hao Huang v Yusuke Takahashi | 2-6,1-6 |
| Challenger Baotou | 2019/08/28 04:40 | Frederico Ferreira Silva v Yusuke Takahashi | 6-3,6-0 |
| Challenger Baotou | 2019/08/27 07:05 | Yusuke Takahashi v Rhett Purcell | 7-5,6-3 |
| ITF M15 Hua Hin | 2019/08/28 03:00 | Kuan-Yi Lee v Cheng-Yu Yu | 2-6,6-2,7-6 |
| ITF M15 Hua Hin | 2019/08/22 05:00 | Kuan-Yi Lee v Tsung-Hao Huang | 6-2,6-4 |
| ITF M15 Hua Hin | 2019/08/21 07:50 | Kuan-Yi Lee v Sanhui Shin | 6-1,6-1 |
| ITF M15 Jakarta | 2019/08/14 05:50 | Sho Shimabukuro v Kuan-Yi Lee | 6-3,6-2 |
| ITF M15 Jakarta | 2019/08/11 03:00 | Vladyslav Orlov v Kuan-Yi Lee | 7-5,4-6,6-4 |
| ITF M15 Jakarta | 2019/08/10 03:00 | Kuan-Yi Lee v Emiliano Maggioli | 6-1,6-1 |
| ITF M15 Jakarta | 2019/08/09 02:30 | Lucas Vuradin v Kuan-Yi Lee | 2-6,7-5,2-6 |
| ITF M15 Jakarta | 2019/08/08 02:30 | Dusty H. Boyer v Kuan-Yi Lee | 2-6,2-6 |