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 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 M25 Sabadell | 2024/09/25 12:05 | Oscar Jose Gutierrez v Roger Pascual Ferra | 6-1,2-6,4-6 |
| ITF M25 Sabadell | 2024/09/24 08:00 | Oscar Jose Gutierrez v Bekkhan Atlangeriev | 6-3,7-6 |
| ITF M25 Sabadell | 2024/09/23 10:00 | Oscar Jose Gutierrez v Rafael Giotis | 6-3,2-6,10-7 |
| ITF M25 Sabadell | 2024/09/22 09:00 | Oscar Jose Gutierrez v Maximo Nagele | 6-0,6-1 |
| ITF M15 Monastir | 2024/09/12 08:30 | Garrett Johns v Oscar Jose Gutierrez | 6-4,6-2 |
| ITF M15 Pontevedra | 2024/10/09 14:35 | Johan Nikles v Iliyan Radulov | 6-1,6-1 |
| ITF M25 Zaragoza | 2024/10/03 12:55 | Iliyan Radulov v Nicholas David Ionel | 6-7,6-7 |
| ITF M25 Zaragoza | 2024/10/02 07:55 | Iliyan Radulov v Ignasi Forcano | 7-5,6-0 |
| ITF M25 Sabadell | 2024/09/28 09:00 | Nicolas Alvarez Varona v Iliyan Radulov | 6-0,6-0 |
| ITF M25 Sabadell | 2024/09/27 11:00 | Ivan Gakhov v Iliyan Radulov | 3-6,6-4,1-6 |
| ITF M25 Sabadell | 2024/09/26 08:55 | Iliyan Radulov v Ryan Nijboer | 7-6,6-7,6-1 |
| ITF M25 Sabadell | 2024/09/25 10:10 | Iliyan Radulov v Samuel Brosset | 7-5,6-1 |
| ITF M25 Sabadell | 2024/09/24 08:00 | Iliyan Radulov v Samuel Brosset | 6-3,2-6,7-10 |