Stadium: Court 1 Round: 14 Ground: Clay
| Challenger Bad Waltersdorf | 2023/09/19 13:10 | Raul Brancaccio v Henri Squire | 7-6,5-7,6-2 |
| Challenger Bad Waltersdorf | 2023/09/18 08:00 | Henri Squire v Marcello Serafini | 6-4,6-2 |
| Challenger Bad Waltersdorf | 2023/09/17 08:00 | Henri Squire v David Pichler | 6-7,6-3,6-4 |
| Challenger Szczecin | 2023/09/12 17:30 | Federico Coria v Henri Squire | 6-4,2-6,6-4 |
| Challenger Szczecin | 2023/09/11 11:40 | Timo Stodder v Henri Squire | 6-7,2-6 |
| Challenger Szczecin | 2023/09/10 12:20 | Jasza Szajrych v Henri Squire | 3-6,4-6 |
| Challenger Tulln | 2023/09/08 11:40 | Flavio Cobolli v Henri Squire | 6-1,6-2 |
| Challenger Tulln | 2023/09/06 15:00 | Lucas Miedler v Henri Squire | 6-4,3-6,4-6 |
| ITF M25 Setubal | 2023/09/21 12:30 | Aidan Mchugh v Tiago Pereira | 6-3,6-3 |
| ITF M25 Setubal | 2023/09/20 09:00 | Afonso Portugal v Tiago Pereira | 0-6,2-6 |
| ITF M25 Sintra | 2023/09/15 10:50 | Goncalo Oliveira v Tiago Pereira | 6-4,3-6,6-2 |
| ITF M25 Sintra | 2023/09/14 11:20 | Michele Ribecai v Tiago Pereira | 3-6,2-6 |
| ITF M25 Sintra | 2023/09/13 10:30 | Tiago Pereira v Martyn Pawelski | 7-6,6-2 |
| ITF M25 Sintra | 2023/09/07 11:50 | Tiago Pereira v Henrique Rocha | 6-7,6-2,3-6 |
| ITF M25 Sintra | 2023/09/06 16:35 | Tiago Pereira v Guillaume Dalmasso | 6-4,6-3 |
| ITF M25 Idanha-A-Nova | 2023/09/01 08:00 | Alberto Barroso Campos v Tiago Pereira | 7-6,7-6 |