Stadion: Court 3 Round: 25 Ground: Clay
| ITF - M25 - Sabadell | 2023/09/26 11:05 | Oscar Jose Gutierrez v Alex M Pujolras | 6-4,2-6,2-6 |
| Challenger - Sevilla | 2023/09/04 16:50 | Inigo C Huegun v Oscar Jose Gutierrez | 7-5,6-2 |
| Challenger - Sevilla | 2023/09/04 13:00 | Alex Lawson v Oscar Jose Gutierrez | 1-6,2-6 |
| ITF - M25 - Oviedo | 2023/08/30 09:15 | Oscar Jose Gutierrez v Facundo Mena | 3-6,2-6 |
| ITF - M25 - Santander | 2023/08/23 09:50 | Sergi Perez Contri v Oscar Jose Gutierrez | 6-4,7-6 |
| ITF - M25 - Santander | 2023/08/22 13:00 | Oscar Jose Gutierrez v Michiel de Krom | 6-2,6-0 |
| Challenger - Liberec | 2023/07/30 08:00 | Kirill Kivattsev v Oscar Jose Gutierrez | 6-2,6-4 |
| ITF - M25 - Denia | 2023/07/26 15:25 | Oscar Jose Gutierrez v Vilius Gaubas | 5-7,6-7 |
| ITF - M25 - Sabadell | 2023/09/28 13:05 | Felix Gill v Iliyan Radulov | 6-3,6-2 |
| ITF - M25 - Sabadell | 2023/09/26 15:30 | Albert Pedrico Kravtsov v Iliyan Radulov | 3-6,1-6 |
| Challenger - Parma | 2023/06/18 08:00 | Bogdan Bobrov v Iliyan Radulov | 4-6,6-2,6-4 |
| ITF - M15 - Kuršumlijska Banja | 2023/06/13 15:55 | Iliyan Radulov v Gabriel Donev | 2-6,4-6 |
| ITF - M15 - Pazardzhik | 2023/05/24 08:45 | Iliyan Radulov v Riccardo Balzerani | 4-6,1-6 |
| ITF - M15 - Pazardzhik | 2023/05/21 12:30 | Iliyan Radulov v Simone Roncalli | 6-4,6-1 |
| ITF - M15 - Pazardzhik | 2023/05/21 07:00 | Denis Klok v Iliyan Radulov | 1-6,1-6 |
| ITF - M15 - Pazardzhik | 2023/05/20 09:45 | Alex Knaff v Iliyan Radulov | 4-6,2-6 |