| ITF Portugal F15 | 08/09 11:05 | 25 | Osorio, Guilherme Wojciechowski v Goncalo Falcao | 3-6,2-6 | |
| ITF Portugal F10 | 07/03 08:00 | 62 | Osorio, Guilherme Wojciechowski v Munoz-Abreu, Jordi | 5-7,7-6,4-6 | |
| ITF Portugal F9 | 06/25 10:00 | 62 | Osorio, Guilherme Wojciechowski v Nkomba, Benard Bruno | 4-6,6-7 | |
| ITF Portugal F9 | 06/24 10:30 | 62 | Osorio, Guilherme Wojciechowski v Rodrigues, Pedro Gabriel | 6-1,6-0 | |
| ITF Portugal F8 Qual | 06/17 10:00 | 62 | Djurdjevic, Bogdan v Osorio, Guilherme Wojciechowski | 7-6,6-3 | |
| ITF Tunisia F36 | 12/14 09:55 | 25 | Trusendi, Walter v Osorio, Guilherme Wojciechowski | 6-2,6-0 | |
| ITF Tunisia F36 | 12/12 10:00 | 44 | Osorio, Guilherme Wojciechowski v Luka Pavlovic | 7-6,6-4 | |
| ITF Tunisia F36 | 12/11 13:00 | 44 | Osorio, Guilherme Wojciechowski v Ben Abdallah, Skander | 6-0,6-2 | |
| ITF Tunisia F35 | 12/05 08:30 | 44 | Javier Barranco Cosano v Osorio, Guilherme Wojciechowski | 6-4,6-1 | |
| ITF Portugal F9 | 07/19 15:40 | 25 | Nuno Borges v Osorio, Guilherme Wojciechowski | 6-3,7-5 | |
| ITF Portugal F6 | 05/18 11:10 | 25 | Osorio, Guilherme Wojciechowski v Wang, Tak Khunn | 3-6,3-6 | |
| ITF Portugal F6 Qual | 05/15 09:00 | 62 | Osorio, Guilherme Wojciechowski v Marcus Walters | 6-3,6-4 | |
| Portugal F4, Singles Qualifying | 05/09 10:00 | 27 | Osorio, Guilherme Wojciechowski v Ojeda Lara, Ricardo | 1-6,1-6 | |
| Portugal F4, Singles Qualifying | 05/03 11:00 | 25 | Addison, Aaron v Osorio, Guilherme Wojciechowski | 3-6,5-7 | |
| ITF Portugal F12 | 09/30 11:00 | 25 | Hernando Ruano, Jorge v Osorio, Guilherme Wojciechowski | 6-1,6-2 | |
| ITF Portugal F12 Qual | 09/28 09:00 | 62 | Osorio, Guilherme Wojciechowski v Antonio, Joao | 7-6,7-6 | |
| ITF Portugal F6 | 05/19 14:50 | - | Antonio, Joao v Osorio, Guilherme Wojciechowski | 2-6,1-6 | |
| ITF Portugal F6 Qual | 05/18 16:00 | - | Mardones, Bruno v Osorio, Guilherme Wojciechowski | 6-7,3-6 | |
| ITF Portugal F6 Qual | 05/17 13:00 | - | Osorio, Guilherme Wojciechowski v Rodrigues, Daniel | 6-3,6-2 | |
| ITF Portugal F5 Qual | 05/11 11:30 | - | Antonio, Joao v Osorio, Guilherme Wojciechowski | 6-3,6-1 | |
| Portugal F4, Singles Qualifying | 05/05 18:00 | - | Osorio, Guilherme Wojciechowski v Santanna, B. | 4-6,1-6 | |
| ITF Portugal F3 Qual | 03/08 10:00 | - | Osorio, Guilherme Wojciechowski v Vallejo, Miguel | 6-0,6-2 | |
| ITF Portugal F2 Qual | 03/02 10:00 | - | Pulgar-Garcia, Jaime v Osorio, Guilherme Wojciechowski | 6-4,6-3 | |
| ITF Portugal F2 Qual | 03/01 14:00 | - | Osorio, Guilherme Wojciechowski v van Der Horst, Tim | 6-2,6-2 | |
| ITF Portugal F2 Qual | 03/01 10:00 | - | Diaz Freire, Gabriel v Osorio, Guilherme Wojciechowski | 6-4,6-0 | |
| ITF Portugal F1 | 02/22 11:30 | - | Osorio, Guilherme Wojciechowski v Semedo, Miguel | 6-2,6-2 | |
| ITF Portugal F9 | 10/06 09:15 | - | Manrique-Velazquez, Diego-Jose v Osorio, Guilherme Wojciechowski | 7-6,6-4 | |
| ITF Portugal F8 Qual | 09/27 09:00 | - | Osorio, Guilherme Wojciechowski v Edan Leshem | 6-4,5-7,4-6 | |
| Portugal F4, Singles Qualifying | 05/14 09:00 | - | Ortega-Olmedo, Roberto v Osorio, Guilherme Wojciechowski | 6-1,6-1 | |
| ITF Portugal F3 Qual | 02/17 10:00 | - | Hirschmueller, Christian v Osorio, Guilherme Wojciechowski | 6-1,7-5 |