Stadium: Quadra 4 Round: 19 Ground: Clay
| Challenger Campinas | 2023/10/01 14:00 | Blaise Bicknell v Matheus C Bueres | 6-2,6-3 |
| Challenger Bogota | 2023/09/26 15:00 | Thiago Agustin Tirante v Blaise Bicknell | 5-7,6-2,7-6 |
| Challenger Bogota | 2023/09/25 17:00 | Blaise Bicknell v Kiranpal Pannu | 7-5,6-7,7-5 |
| Challenger Bogota | 2023/09/24 18:15 | Blaise Bicknell v Marcelo Zormann | 6-4,3-6,6-4 |
| Davis Cup | 2023/09/15 11:20 | Hady Habib v Blaise Bicknell | 7-6,6-1 |
| Challenger Istanbul | 2023/09/07 07:30 | Dino Prizmic v Blaise Bicknell | 4-6,6-3,6-2 |
| Challenger Istanbul | 2023/09/05 09:40 | Blaise Bicknell v Matteo Martineau | 6-7,7-6,6-3 |
| Challenger Istanbul | 2023/09/04 08:30 | Vladyslav Orlov v Blaise Bicknell | 0-6,1-6 |
| Challenger Antofagasta | 2023/09/19 19:40 | Pedro Sakamoto v Francisco Comesana | 6-0,5-7,4-6 |
| Challenger Antofagasta | 2023/09/18 14:55 | Pedro Sakamoto v Victor Lilov | 6-1,6-4 |
| Challenger Antofagasta | 2023/09/17 18:00 | Mateus Alves v Pedro Sakamoto | 6-7,4-6 |
| Challenger Santa Cruz | 2023/09/15 18:30 | Juan Manuel Cerundolo v Pedro Sakamoto | 7-5,6-4 |
| Challenger Santa Cruz | 2023/09/14 19:00 | Pedro Sakamoto v Joao Lucas Reis da Silva | 4-6,7-6,6-2 |
| Challenger Santa Cruz | 2023/09/12 23:00 | Tristan Boyer v Pedro Sakamoto | 4-6,4-6 |
| Challenger Lima | 2023/08/23 15:00 | Murkel Dellien v Pedro Sakamoto | 5-7,6-0,6-0 |
| Challenger Lima | 2023/08/22 18:45 | Guido Ivan Justo v Pedro Sakamoto | 4-6,6-7 |