Stadium: Court 2 Round: 24 Ground: Hardcourt outdoor
| ITF Australia F7 | 2015/10/09 02:30 | Zhe Li v Akira Santillan | 6-4,6-2 |
| ITF Japan F3 | 2015/03/25 02:35 | Akira Santillan v Zhe Li | 6-4,6-2 |
| Challenger Granby | 2019/07/26 15:00 | Zhe Li v Yasutaka Uchiyama | 7-6,4-6,1-6 |
| Challenger Granby | 2019/07/25 14:00 | Cem Ilkel v Zhe Li | 6-4,6-7,5-7 |
| Challenger Granby | 2019/07/23 16:45 | Takanyi Garanganga v Zhe Li | 6-7,6-7 |
| Challenger Gatineau | 2019/07/15 18:30 | Zhe Li v Maximilian Neuchrist | 1-6,1-6 |
| Challenger Winnipeg | 2019/07/12 20:15 | Zhe Li v Norbert Gombos | 4-6,2-6 |
| Challenger Winnipeg | 2019/07/11 20:45 | Bernard Tomic v Zhe Li | 6-1,6-7,4-6 |
| Challenger Winnipeg | 2019/07/10 21:10 | Joao Menezes v Zhe Li | 3-6,2-6 |
| Wimbledon | 2019/06/24 15:45 | Zhe Li v Dustin Brown | 6-7,3-6 |
| Challenger Lexington | 2019/08/02 16:35 | JC Aragone v Akira Santillan | 7-6,7-6 |
| Challenger Lexington | 2019/08/01 15:25 | Borna Gojo v Akira Santillan | 6-7,6-4,2-6 |
| Challenger Lexington | 2019/07/31 17:50 | Vasil Kirkov v Akira Santillan | 4-6,3-6 |
| Challenger Granby | 2019/07/24 16:10 | Akira Santillan v Maximilian Neuchrist | 0-6,7-6,4-6 |
| Challenger Gatineau | 2019/07/15 16:05 | Akira Santillan v Carlos Gomez-Herrera | 6-3,3-6,1-6 |
| Wimbledon | 2019/06/26 10:00 | Ruben Bemelmans v Akira Santillan | 6-7,6-3,12-10 |
| Wimbledon | 2019/06/24 11:45 | Jurij Rodionov v Akira Santillan | 3-6,1-6 |
| Challenger Shymkent 2 | 2019/06/11 08:15 | Nicola Kuhn v Akira Santillan | 1-6,7-5,6-3 |