Stadium: Court 13 Round: 26 Ground: Hardcourt outdoor
| ITF M25 Sintra | 2023/09/13 09:00 | Trey Hilderbrand v Duarte Vale | 4-6,3-6 |
| ITF M25 Sintra | 2023/09/08 09:30 | Sebastian Fanselow v Duarte Vale | 6-4,6-1 |
| ITF M25 Sintra | 2023/09/07 12:50 | Pedro Araujo v Duarte Vale | 6-4,5-7,4-6 |
| ITF M25 Sintra | 2023/09/06 15:40 | Goncalo Falcao v Duarte Vale | 1-6,4-6 |
| ITF M25 Idanha-A-Nova | 2023/09/01 09:35 | Duarte Vale v Dan Added | 2-6,3-6 |
| ITF M25 Idanha-A-Nova | 2023/08/31 11:45 | Duarte Vale v Pierre Delage | 6-4,6-3 |
| ITF M25 Idanha-A-Nova | 2023/08/30 08:00 | Duarte Vale v Max Cunat | 6-2,6-4 |
| ITF M25 Idanha-A-Nova | 2023/08/22 08:00 | Gabriele Bosio v Duarte Vale | 7-5,6-1 |
| 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 |
| ITF M25 Kramsach | 2023/07/30 10:00 | Gerard Campana Lee v Kalin Ivanovski | 2-6,2-6 |
| ITF M25 Kramsach | 2023/07/29 10:00 | Mathys Erhard v Kalin Ivanovski | 6-4,2-6,2-6 |
| ITF M25 Kramsach | 2023/07/28 09:00 | Sandro Kopp v Kalin Ivanovski | 6-7,4-6 |