Stadium: Grandstand Court Round: 26 Ground: Hardcourt indoor
| Challenger - Calgary | 2020/02/26 00:10 | Manuel Guinard v Tobias Simon | 7-6,6-7,6-7 |
| Challenger - Calgary | 2020/02/24 17:35 | Tobias Simon v Taha Baadi | 7-6,6-2 |
| Challenger - Drummondville | 2020/02/19 15:00 | Sebastian Korda v Tobias Simon | 6-3,4-6,7-6 |
| Challenger - Drummondville | 2020/02/17 16:00 | Razvan Baiant v Tobias Simon | 2-6,2-6 |
| Challenger - Launceston | 2020/02/05 02:40 | Tobias Simon v Kimmer Coppejans | 4-6,7-6,3-6 |
| Challenger - Launceston | 2020/02/03 03:30 | Tobias Simon v Alexander Crnokrak | 6-4,7-6 |
| Challenger - Burnie | 2020/01/27 03:40 | Michail Pervolarakis v Tobias Simon | 6-3,6-4 |
| ITF M25 - Rancho Santa Fe | 2020/01/16 19:50 | Tobias Simon v Emilio Nava | 6-7,6-7 |
| 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 |
| 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 |