Stadium: Center Court Round: 25 Ground: Hardcourt outdoor
| Challenger Tyler | 2023/06/05 23:05 | Denis Yevseyev v Mikhail Kukushkin | 6-7,2-6 |
| Challenger Little Rock | 2023/05/30 20:25 | Alex Michelsen v Denis Yevseyev | 4-6,6-3,7-5 |
| ATP Geneva | 2023/05/20 11:30 | Alessandro Giannessi v Denis Yevseyev | 3-6,6-4,6-2 |
| Challenger Oeiras | 2023/05/14 15:30 | Daniel Rodrigues v Denis Yevseyev | 6-4,2-6,6-4 |
| Challenger Prague Qual | 2023/05/07 08:30 | Denis Yevseyev v Martin Damm | 3-6,2-6 |
| Challenger Prague | 2023/04/30 14:45 | Federico Gaio v Denis Yevseyev | 6-0,6-7,6-3 |
| Challenger Savannah | 2023/04/25 14:00 | Martin Damm v Denis Yevseyev | 6-1,6-4 |
| Challenger Morelos | 2023/04/19 18:10 | Mark Lajal v Denis Yevseyev | 7-5,6-1 |
| Challenger Tyler | 2023/06/05 20:40 | Joao Lucas Reis da Silva v Adam Neff | 6-4,2-6,3-6 |
| Challenger Little Rock | 2023/06/01 18:40 | Joao Lucas Reis da Silva v Adam Walton | 6-3,6-7,4-6 |
| Challenger Little Rock | 2023/05/30 15:00 | Maks Kasnikowski v Joao Lucas Reis da Silva | 2-6,3-6 |
| 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 |