Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| Challenger Little Rock | 2023/05/29 15:00 | Maks Kasnikowski v Omni Kumar | 6-4,7-5 |
| Challenger Little Rock | 2023/05/28 15:00 | Maks Kasnikowski v Rubin Statham | 6-3,6-7,6-4 |
| Challenger Skopje | 2023/05/23 10:00 | Dragos Nicolae Madaras v Maks Kasnikowski | 7-6,6-1 |
| Challenger Skopje | 2023/05/22 10:30 | Maks Kasnikowski v Duje Ajdukovic | 5-7,7-5,7-6 |
| Challenger Skopje | 2023/05/21 12:15 | Maks Kasnikowski v Blaz Rola | 1-6,7-5,7-5 |
| ITF M15 - Kursumlijska Banja | 2023/05/05 09:25 | Maks Kasnikowski v Elliot Benchetrit | 6-4,6-7,5-7 |
| ITF M15 - Kursumlijska Banja | 2023/05/04 11:40 | Maks Kasnikowski v Petr Nesterov | 7-6,6-1 |
| ITF M15 - Kursumlijska Banja | 2023/05/03 14:10 | Maks Kasnikowski v Kristijan Juhas | 7-5,6-4 |
| Challenger Coquimbo | 2023/05/06 18:00 | Joao Lucas Reis da Silva v Matheus P De Almeida | 6-7,7-6,4-6 |
| Challenger Coquimbo | 2023/05/05 18:40 | Joao Lucas Reis da Silva v Roman Andres Burruchaga | 6-2,6-4 |
| Challenger Coquimbo | 2023/05/04 16:10 | Nick Hardt v Joao Lucas Reis da Silva | 3-6,7-6,1-6 |
| Challenger Coquimbo | 2023/05/03 18:20 | Pedro Boscardin Dias v Joao Lucas Reis da Silva | 2-6,2-6 |
| Challenger Coquimbo | 2023/05/01 18:40 | Eduardo Ribeiro v Joao Lucas Reis da Silva | 2-6,3-6 |
| Challenger Buenos Aires | 2023/04/27 16:15 | Hernan Casanova v Joao Lucas Reis da Silva | 6-1,6-7,6-4 |
| Challenger Buenos Aires | 2023/04/25 13:00 | Joao Lucas Reis da Silva v Juan Pablo Ficovich | 6-2,7-5 |
| Challenger Morelos | 2023/04/18 16:30 | Christian Langmo v Joao Lucas Reis da Silva | 7-6,6-2 |