Stadium: Court 1 Round: 27 Ground: Hardcourt outdoor
| ITF M25 Setubal | 2023/09/21 12:30 | Clement Chidekh v Jaime Faria | 4-6,5-7 |
| ITF M25 Setubal | 2023/09/20 11:45 | Jaime Faria v Stuart Parker | 7-6,6-2 |
| ITF M25 Sintra | 2023/09/15 09:00 | Henrique Rocha v Jaime Faria | 6-3,1-6,6-3 |
| ITF M25 Sintra | 2023/09/14 10:35 | Philip Hjorth v Jaime Faria | 3-6,3-6 |
| ITF M25 Sintra | 2023/09/13 10:50 | Lorenzo Claverie v Jaime Faria | 2-6,6-7 |
| ITF M25 Sintra | 2023/09/10 09:30 | Jaime Faria v Harry Wendelken | 6-3,2-6,6-7 |
| ITF M25 Sintra | 2023/09/09 10:30 | Jaime Faria v Sebastian Fanselow | 6-3,3-6,6-3 |
| ITF M25 Sintra | 2023/09/08 09:25 | Trey Hilderbrand v Jaime Faria | 2-6,3-6 |
| ITF M25 Setubal | 2023/09/21 12:30 | Francisco Rocha v Kalin Ivanovski | 6-7,3-6 |
| ITF M25 Setubal | 2023/09/19 12:20 | Sascha Gueymard Wayenburg v Kalin Ivanovski | 4-6,4-6 |
| ITF M25 Sintra | 2023/09/14 09:00 | Duarte Vale v Kalin Ivanovski | 7-6,6-4 |
| ITF M25 Sintra | 2023/09/13 14:15 | Marcus Walters v Kalin Ivanovski | 4-6,6-7 |
| Challenger Cassis | 2023/09/04 11:15 | Kalin Ivanovski v Federico Gaio | 6-1,3-6,4-6 |
| Challenger Mallorca | 2023/08/30 20:05 | Joao Sousa v Kalin Ivanovski | 6-4,7-6 |
| Challenger Grodzisk Mazowiecki | 2023/08/15 13:35 | Marius Copil v Kalin Ivanovski | 6-4,1-6,6-4 |
| Challenger Banja Luka | 2023/08/08 10:30 | Clement Tabur v Kalin Ivanovski | 7-6,7-6 |