Stadium: Court 1 Round: 14 Ground: Clay
| Challenger Oeiras | 2023/05/16 10:10 | Jan Choinski v Alessandro Giannessi | 6-3,4-6,6-4 |
| Challenger Oeiras | 2023/05/15 09:00 | Alessandro Giannessi v Daniel Michalski | 6-4,6-4 |
| Challenger Oeiras | 2023/05/14 10:25 | Alessandro Giannessi v Alberto Barroso Campos | 6-1,6-3 |
| Challenger Francavilla | 2023/05/10 11:20 | Benoit Paire v Alessandro Giannessi | 7-5,7-5 |
| Challenger Francavilla | 2023/05/09 09:00 | Alessandro Giannessi v Marco Trungelliti | 3-6,6-3,6-4 |
| Challenger Cagliari | 2023/05/04 11:45 | Alessandro Giannessi v Thanasi Kokkinakis | 4-6,2-6 |
| Challenger Cagliari | 2023/05/03 10:25 | Alessandro Giannessi v Francesco Passaro | 3-6,7-6,6-4 |
| Challenger Cagliari | 2023/05/02 08:30 | Alessandro Giannessi v Alexander Erler | 7-5,6-1 |
| 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 Morelos | 2023/04/18 16:30 | Naoki Nakagawa v Denis Yevseyev | 6-7,6-4,2-6 |
| Challenger Leon | 2023/04/11 21:05 | Denis Yevseyev v Benjamin Lock | 5-7,5-7 |
| Challenger San Luis Potosi | 2023/04/07 17:25 | Dominik Koepfer v Denis Yevseyev | 6-3,6-2 |