| UTR Pro Tennis Series California | 01/02 18:40 | - | Osorio, Guilherme Wojciechowski v Huang, Austen | 6-3,6-2 | |
| UTR Pro Tennis Series California | 01/01 19:00 | - | Osorio, Guilherme Wojciechowski v Luke Casper | 3-6,6-3,6-1 | |
| UTR Pro Tennis Series California | 01/01 02:40 | - | Osorio, Guilherme Wojciechowski v Sacchitt Sharrma | View | |
| UTR Pro Tennis Series California | 12/28 21:30 | - | Hugo Hashimoto v Osorio, Guilherme Wojciechowski | 6-4,6-2 | |
| UTR Pro Tennis Series California | 12/27 20:02 | - | Emin Torlic v Osorio, Guilherme Wojciechowski | 1-6,0-6 | |
| UTR Pro Tennis Series California | 12/26 22:30 | - | Jacob Bullard v Osorio, Guilherme Wojciechowski | 5-7,1-6 | |
| ITF M15 Idanha-a-Nova | 07/09 09:00 | 54 | Osorio, Guilherme Wojciechowski v Sean Hodkin | 6-7,6-4,4-10 | |
| ITF M15 Idanha-a-Nova | 07/08 09:00 | 54 | Osorio, Guilherme Wojciechowski v Almeida, Eduardo Lobo Da Rosa de | 6-1,6-0 | |
| ITF USA F24 | 09/12 16:30 | 25 | Osorio, Guilherme Wojciechowski v Keegan Smith | 6-7,3-6 | |
| ITF Portugal F14 | 08/09 10:30 | 26 | Osorio, Guilherme Wojciechowski v Frederico F Silva | 0-6,2-6 | |
| ITF Portugal F14 | 08/07 11:00 | 25 | Mark Whitehouse v Osorio, Guilherme Wojciechowski | 6-7,6-4,4-6 | |
| ITF Portugal F13 | 08/04 10:00 | 28 | Daniel Batista v Osorio, Guilherme Wojciechowski | 6-3,7-6 | |
| ITF Portugal F13 | 08/03 09:30 | 27 | Osorio, Guilherme Wojciechowski v Vernier, Michel | 6-2,7-5 | |
| ITF Portugal F13 | 08/02 10:00 | 26 | Cacao, Tiago v Osorio, Guilherme Wojciechowski | 2-6,6-4,4-6 | |
| ITF Portugal F13 | 07/31 10:00 | 25 | Goncalo Falcao v Osorio, Guilherme Wojciechowski | 1-6,2-6 | |
| ITF Portugal F11 | 07/04 14:15 | 25 | Vivero Gonzalez, Pablo v Osorio, Guilherme Wojciechowski | 5-7,6-2,6-4 | |
| ITF Portugal F11 Qual | 07/03 08:30 | 62 | Elio Jose Ribeiro Lago v Osorio, Guilherme Wojciechowski | 4-6,2-6 | |
| ITF Portugal F11 Qual | 07/02 11:00 | 62 | Roman Mayorga, Maximiliano v Osorio, Guilherme Wojciechowski | 2-6,1-6 | |
| ITF Portugal F10 | 06/25 09:30 | 62 | Alexander Donski v Osorio, Guilherme Wojciechowski | 2-6,7-5,6-4 | |
| ITF Portugal F10 | 06/24 12:00 | 62 | Luis Lamelas, Manuel v Osorio, Guilherme Wojciechowski | 1-6,0-6 | |
| ITF Portugal F10 | 06/23 15:00 | 62 | van Veggel, Renato v Osorio, Guilherme Wojciechowski | 1-6,1-6 | |
| ITF USA F31 | 09/21 17:00 | 26 | Osorio, Guilherme Wojciechowski v Fawcett, Tom | Walkover | |
| ITF USA F31 | 09/20 20:45 | 25 | Iftikhar, Samir v Osorio, Guilherme Wojciechowski | 2-6,1-6 | |
| ITF USA F31 | 09/20 20:00 | - | Iftikhar, Samir v Osorio, Guilherme Wojciechowski | 2-6,1-6 | |
| ITF USA F31 | 09/18 18:00 | 60 | Osorio, Guilherme Wojciechowski v Wattanakul, Pol | 6-2,6-0 | |
| ITF USA F31 | 09/17 19:00 | 60 | Osorio, Guilherme Wojciechowski v Lopez, Luis Humberto | 6-1,6-4 | |
| ITF USA F31 | 09/16 18:45 | 60 | Pervolarakis, Michail v Osorio, Guilherme Wojciechowski | Retired | |
| ITF Portugal F16 | 08/14 09:00 | 62 | Osorio, Guilherme Wojciechowski v Ryan Peniston | 3-6,1-6 | |
| ITF Portugal F16 | 08/13 10:00 | 62 | Carr, Simon v Osorio, Guilherme Wojciechowski | 4-6,5-7 | |
| ITF Portugal F16 | 08/12 10:00 | 62 | Montalvo Hidalgo, Manuel v Osorio, Guilherme Wojciechowski | 2-6,3-6 |