Stadium: Court 3 Round: 25 Ground: Hardcourt outdoor
| ITF M25 Sharm El Sheikh | 2023/09/21 09:50 | Kris Van Wyk v Andrea Guerrieri | 6-1,6-1 |
| ITF M25 Sharm El Sheikh | 2023/09/20 07:00 | Daniil Ostapenkov v Andrea Guerrieri | 6-7,0-6 |
| ITF M25 Pozzuoli | 2023/09/14 11:10 | Alessandro Pecci v Andrea Guerrieri | 7-6,6-3 |
| ITF M25 Pozzuoli | 2023/09/12 10:30 | Andrea Colombo v Andrea Guerrieri | 0-6,2-6 |
| ITF M15 Monastir | 2023/09/08 08:00 | Andrea Guerrieri v Peter Bertran | 2-6,2-6 |
| ITF M15 Monastir | 2023/09/07 08:00 | Andrea Guerrieri v Aleksandr Lobanov | 7-5,6-4 |
| ITF M15 Monastir | 2023/09/05 08:00 | Andrea Guerrieri v Saveliy Ivanov | 6-3,6-3 |
| ITF M25 Aldershot | 2023/08/17 09:00 | Andrea Guerrieri v Toby Samuel | 3-6,0-6 |
| Challenger Lisbon | 2023/10/01 11:00 | Pedro Araujo v Carlos Sanchez Jover | 3-6,1-6 |
| Challenger Braga | 2023/09/24 14:10 | Pedro Araujo v Giovanni Fonio | 1-6,7-5,5-7 |
| ITF M25 Setubal | 2023/09/21 12:30 | Pedro Araujo v Henrique Rocha | 4-6,4-6 |
| ITF M25 Setubal | 2023/09/20 10:35 | Pedro Araujo v Fabio Coelho | 6-2,6-3 |
| ITF M25 Sintra | 2023/09/15 09:00 | Pedro Araujo v Martin Damm | 3-6,4-6 |
| ITF M25 Sintra | 2023/09/14 08:50 | Preston Brown v Pedro Araujo | 2-6,1-6 |
| ITF M25 Sintra | 2023/09/13 10:15 | Adan Freire Da Silva v Pedro Araujo | 6-3,1-6,3-6 |
| ITF M25 Sintra | 2023/09/07 12:50 | Pedro Araujo v Duarte Vale | 6-4,5-7,4-6 |