Stadium: Court 8 Round: 44 Ground: Hardcourt outdoor
| ITF M25 Quinta Do Lago | 2024/03/03 10:00 | Tomas Almeida v Guilherme Valdoleiros | 7-6,6-4 |
| Challenger Maia | 2023/11/26 16:55 | Alexey Vatutin v Guilherme Valdoleiros | 6-4,6-0 |
| ITF M25 Vale Do Lobo | 2023/11/12 11:00 | Mikel Martinez v Guilherme Valdoleiros | 6-0,6-1 |
| ITF M25 Tavira | 2023/10/16 08:30 | Eero Vasa v Guilherme Valdoleiros | 6-4,6-2 |
| ITF M25 Tavira | 2023/10/15 09:00 | Jamie Krattiger v Guilherme Valdoleiros | 3-6,2-6 |
| ITF M25 Tavira | 2023/10/09 11:30 | Jack Molloy v Guilherme Valdoleiros | 6-4,6-2 |
| ITF M25 Tavira | 2023/10/08 11:30 | Rafael Mazon-Hernandez v Guilherme Valdoleiros | 3-6,7-6,3-10 |
| ITF M25 Setubal | 2023/09/19 09:00 | Rafael I Luque v Guilherme Valdoleiros | 6-1,6-2 |
| ITF M25 Quinta Do Lago | 2024/03/05 10:00 | Tiago Pereira v Miguel Simao | 6-1,6-0 |
| ITF M25 Sintra | 2023/09/03 08:00 | Fedor Sosedkin v Miguel Simao | 6-1,6-2 |
| ITF M25 Idanha-A-Nova | 2023/08/27 10:00 | Miguel Simao v Sergio Davila Godoy | 0-6,0-6 |
| ITF M25 Idanha-A-Nova | 2023/08/20 10:00 | Gabriel Elicha Navas v Miguel Simao | 6-0,6-2 |
| ITF M25 Cordoba | 2023/06/04 14:00 | Miguel Simao v Sergi Fita Juan | 0-6,1-6 |
| ITF M25 Vila Real de Santo Antonio | 2023/02/12 09:00 | Alvaro Peiro Serrano v Miguel Simao | 6-1,6-1 |
| ITF M25 Vila Real de Santo Antonio | 2023/02/05 10:00 | Miguel Simao v Tomas Cortez | 3-6,3-6 |
| ITF M25 Quinta Do Lago | 2022/03/21 13:30 | Miguel Simao v Gabriele Moghini | 1-6,2-6 |