Stadium: Cancha 3 Round: 25 Ground: Clay
| Challenger - Prostějov | 2023/06/05 09:35 | Pedro Sakamoto v Hynek Barton | 2-6,4-6 |
| Challenger - Prostějov | 2023/06/04 11:25 | Lorenzo Giustino v Pedro Sakamoto | 6-4,6-7,6-7 |
| ITF - M25 Jablonec Nad Nisou | 2023/05/30 07:55 | Pedro Sakamoto v Noah Schlagenhauf | 4-6,6-3,5-10 |
| ITF - M25 Jablonec Nad Nisou | 2023/05/29 08:00 | Pedro Sakamoto v Sebastian Buehler | 6-1,6-1 |
| ITF - M25 Bodrum | 2023/05/25 07:00 | Rudolf Molleker v Pedro Sakamoto | 6-4,6-1 |
| ITF - M25 Bodrum | 2023/05/24 07:00 | Pedro Sakamoto v Filip Peliwo | 7-5,6-0 |
| ITF - M25 Bodrum | 2023/05/23 07:45 | Pedro Sakamoto v Bora Sengul | 6-4,7-5 |
| ITF - M15 Kalmar | 2023/05/17 08:00 | Nicolas Kobelt v Pedro Sakamoto | 6-3,7-5 |
| Challenger - Palmas del Mar | 2023/06/13 15:00 | Patrick Kypson v Alexis Galarneau | 3-6,0-6 |
| Challenger - Tyler | 2023/06/04 17:25 | Patrick Kypson v Rubin Statham | 6-7,6-4,6-7 |
| French Open | 2023/05/28 09:00 | Patrick Kypson v Radu Albot | 3-6,2-6,6-4,1-6 |
| Challenger - Savannah | 2023/04/29 17:30 | Patrick Kypson v Facundo Diaz Acosta | 3-6,6-4,4-6 |
| Challenger - Savannah | 2023/04/28 17:45 | Patrick Kypson v Nicolas Kicker | 6-2,6-3 |
| Challenger - Savannah | 2023/04/26 15:00 | Patrick Kypson v Evan Zhu | 4-6,6-2,6-1 |
| Challenger - Savannah | 2023/04/24 18:45 | Alex Michelsen v Patrick Kypson | 6-4,3-6,6-7 |
| Challenger - Tallahassee | 2023/04/19 23:25 | Patrick Kypson v Zizou Bergs | 2-6,2-6 |