Stadium: Stadium Round: 26 Ground: Hardcourt outdoor
| Challenger Winnipeg | 2023/08/15 16:00 | Gabriel Diallo v Enzo Couacaud | 4-6,6-2,7-6 |
| ATP Toronto | 2023/08/09 19:00 | Gabriel Diallo v Alex De Minaur | 4-6,5-7 |
| ATP Toronto | 2023/08/08 21:45 | Gabriel Diallo v Daniel Evans | 7-6,7-5 |
| ATP Los Cabos | 2023/08/01 02:35 | Gabriel Diallo v Gijs Brouwer | 2-6,6-4,2-6 |
| ATP Atlanta | 2023/07/23 15:00 | Gabriel Diallo v Jason Jung | 6-4,5-7,6-7 |
| ATP Atlanta | 2023/07/22 14:00 | Gabriel Diallo v Bradley Klahn | 6-3,6-2 |
| ATP Newport | 2023/07/18 20:10 | Gabriel Diallo v Kevin Anderson | 3-6,2-6 |
| Wimbledon | 2023/06/28 10:00 | Matteo Gigante v Gabriel Diallo | 6-4,6-4 |
| Challenger Winnipeg | 2023/08/14 20:00 | Alexis Galarneau v Mattia Bellucci | 6-7,7-6,3-6 |
| Challenger Porto | 2023/07/31 14:20 | Joao Sousa v Mattia Bellucci | 6-7,6-4,6-4 |
| Challenger - Segovia | 2023/07/24 15:30 | Ryan Peniston v Mattia Bellucci | 6-4,6-4 |
| Challenger Pozoblanco | 2023/07/19 17:00 | Mattia Bellucci v Dan Added | 6-7,6-7 |
| Challenger Pozoblanco | 2023/07/17 21:30 | Mattia Bellucci v Louis Wessels | 7-6,6-3 |
| Challenger Milan | 2023/07/03 13:00 | Thiago Agustin Tirante v Mattia Bellucci | 6-3,7-6 |
| Wimbledon | 2023/06/29 11:00 | Dominic Stephan Stricker v Mattia Bellucci | 6-3,1-6,6-3,6-4 |
| Wimbledon | 2023/06/28 13:00 | Raphael Collignon v Mattia Bellucci | 4-6,4-6 |