Stadium: Court 4 Round: 26 Ground: Clay
| Challenger Sewilla | 2022/09/04 14:00 | Pablo Llamas Ruiz v Oscar Jose Gutierrez | 3-6,6-7 |
| ITF - Santander M25 | 2022/08/25 12:30 | Oscar Jose Gutierrez v Pablo Llamas Ruiz | 6-3,7-6 |
| ITF - Madryt M25 | 2021/09/16 11:45 | Pablo Llamas Ruiz v Oscar Jose Gutierrez | 6-3,6-3 |
| ITF - Palmanova M25 | 2023/03/15 12:15 | Pablo Llamas Ruiz v Gianmarco Ferrari | 7-6,6-1 |
| ITF - Faro M25 | 2023/02/22 09:55 | Sergi Perez Contri v Pablo Llamas Ruiz | 6-4,6-4 |
| ITF - Vila Real de Santo Antonio M25 | 2023/02/18 12:15 | Pablo Llamas Ruiz v Federico Gaio | 6-3,6-7,3-6 |
| ITF - Vila Real de Santo Antonio M25 | 2023/02/17 10:00 | Christian Sigsgaard v Pablo Llamas Ruiz | 6-4,2-6,2-6 |
| ITF - Vila Real de Santo Antonio M25 | 2023/02/16 11:10 | Julio Cesar Porras v Pablo Llamas Ruiz | 5-7,7-5,4-6 |
| ITF - Vila Real de Santo Antonio M25 | 2023/02/15 11:45 | Duarte Vale v Pablo Llamas Ruiz | 3-6,4-6 |
| Challenger Tenerife | 2023/02/10 15:55 | Matteo Gigante v Pablo Llamas Ruiz | 6-2,6-4 |
| Challenger Maspalomas | 2022/12/03 12:00 | Dusan Lajovic v Pablo Llamas Ruiz | 3-6,6-2,6-2 |
| ITF - Palmanova M25 | 2023/03/15 14:10 | Oscar Jose Gutierrez v Bruno P Navarro | 7-6,6-4 |
| ITF - Torello M25 | 2023/03/02 13:10 | Edas Butvilas v Oscar Jose Gutierrez | 6-4,6-2 |
| ITF - Torello M25 | 2023/03/01 12:40 | Paul Cayre v Oscar Jose Gutierrez | 6-2,4-6,4-6 |
| Challenger Rovereto | 2023/02/19 12:05 | Alejandro Moro Canas v Oscar Jose Gutierrez | 6-4,6-0 |
| ITF - Vila Real de Santo Antonio M25 | 2023/02/16 11:25 | Federico Gaio v Oscar Jose Gutierrez | 4-6,6-4,6-2 |
| ITF - Vila Real de Santo Antonio M25 | 2023/02/15 15:20 | Timo Legout v Oscar Jose Gutierrez | 4-6,4-6 |
| Challenger Tenerife | 2023/02/09 13:05 | Stefano Travaglia v Oscar Jose Gutierrez | 6-0,6-0 |
| Challenger Tenerife | 2023/02/07 12:50 | Oscar Jose Gutierrez v Marek Gengel | 1-6,6-0,6-3 |