Estádio: Court 5 Round: 25 Ground: Hardcourt outdoor
| Challenger - Calgary | 2020/02/28 21:55 | Maxime Cressy v Yusuke Takahashi | 4-6,7-6,6-4 |
| Challenger - Calgary | 2020/02/27 17:00 | Tobias Simon v Yusuke Takahashi | 4-6,6-7 |
| Challenger - Calgary | 2020/02/26 01:25 | Yusuke Takahashi v Tatsuma Ito | 6-3,6-3 |
| Challenger - Calgary | 2020/02/24 19:25 | Yusuke Takahashi v Quentin Robert | 6-4,6-4 |
| Challenger - Drummondville | 2020/02/16 16:20 | Liam Caruana v Yusuke Takahashi | 7-5,6-3 |
| ITF - M25 Nonthaburi | 2020/01/30 02:30 | Chun Hsin Tseng v Yusuke Takahashi | 1-6,6-4,7-6 |
| ITF - M25 Nonthaburi | 2020/01/28 06:15 | Krittin Koaykul v Yusuke Takahashi | 1-6,3-6 |
| Challenger - Pune | 2019/11/13 09:30 | Steven Diez v Yusuke Takahashi | 6-2,6-2 |
| ITF - M15 Heraklion | 2020/11/21 13:00 | Kalin Ivanovski v Adrian Andreev | 1-6,4-6 |
| ITF - M15 Heraklion | 2020/11/19 09:35 | Lucas Gerch v Kalin Ivanovski | 6-7,6-7 |
| ITF - M15 Heraklion | 2020/11/18 12:30 | Kalin Ivanovski v Stefan Palosi | 7-5,6-2 |
| ITF - M15 Heraklion | 2020/11/12 11:00 | Stuart Parker v Kalin Ivanovski | 6-2,6-0 |
| ITF - M15 Heraklion | 2020/11/01 10:00 | Kalin Ivanovski v Nicholas David Ionel | 4-6,2-6 |
| Adriatic Tennis Series | 2020/06/16 14:30 | Carlos Gomez-Herrera v Kalin Ivanovski | 6-2,6-0 |
| ITF - M15 Porec | 2020/03/09 09:00 | Pawel Juszczak v Kalin Ivanovski | 1-6,6-3,10-3 |
| ITF - M15 Porec | 2020/03/08 09:10 | Obrad Markovski v Kalin Ivanovski | 3-6,1-6 |