Stadium: Court 16 Round: 26 Ground: Clay
| ITF M25 Zaragoza | 2023/10/03 10:30 | Oscar Jose Gutierrez v Iliyan Radulov | 1-6,6-7 |
| ITF M15 Madrid | 2024/12/04 08:25 | Sergio Planella Hernandez v Oscar Jose Gutierrez | 1-6,6-4,1-6 |
| ITF M15 Madrid | 2024/12/03 08:30 | Oscar Jose Gutierrez v Mario Mansilla Diez | 6-2,6-1 |
| ITF M15 Madrid | 2024/12/01 09:00 | Oscar Jose Gutierrez v Rodrigo Mora Clement | 6-0,6-1 |
| Challenger Rovereto | 2024/11/17 16:00 | Michael Agwi v Oscar Jose Gutierrez | 6-1,7-6 |
| ITF M15 Valencia | 2024/11/12 09:00 | Alejo Sanchez Quilez v Oscar Jose Gutierrez | 2-6,7-6,6-1 |
| ITF M15 Pontevedra | 2024/10/10 09:00 | Oscar Jose Gutierrez v Adrien Gobat | 4-6,3-6 |
| ITF M15 Pontevedra | 2024/10/09 08:30 | Ian Luca Cervantes Tomas v Oscar Jose Gutierrez | 4-6,1-6 |
| ITF M25 Zaragoza | 2024/10/02 10:00 | Miguel Damas v Oscar Jose Gutierrez | 6-4,7-6 |
| ITF M15 Madrid | 2024/12/04 10:45 | Iliyan Radulov v Lucas Bouquet | 6-2,6-4 |
| ITF M15 Madrid | 2024/12/01 10:00 | Iliyan Radulov v Darwin Blanch | 6-4,7-5 |
| ITF M15 Madrid | 2024/11/30 10:00 | Adan Freire Da Silva v Iliyan Radulov | 2-6,4-6 |
| ITF M15 Madrid | 2024/11/29 11:50 | Andrea Guerrieri v Iliyan Radulov | 3-6,4-6 |
| ITF M15 Madrid | 2024/11/28 09:00 | Iliyan Radulov v Andres Martin | 6-4,6-1 |
| Challenger Montemar | 2024/11/21 11:15 | Denis Yevseyev v Iliyan Radulov | 6-0,6-2 |
| ITF M15 Valencia | 2024/11/12 09:00 | Miguel Damas v Iliyan Radulov | 7-6,2-6,7-5 |
| ITF M25 Sintra | 2024/10/18 14:00 | Gauthier Onclin v Iliyan Radulov | 5-7,6-0,6-3 |