Stadium: Court 3 Round: 26 Ground: Hardcourt outdoor
| Puerto Vallarta, Mexico | 2019/04/29 19:45 | Ortega-Olmedo, Roberto v Yusuke Takahashi | 5-7,1-6 |
| Challenger Leon | 2019/04/22 17:30 | Ortega-Olmedo, Roberto v Yusuke Takahashi | 6-4,6-4 |
| ITF - M25 Loulé | 2021/10/13 11:00 | Ortega-Olmedo, Roberto v Lipovsek Puches, Tomas | 6-1,6-1 |
| Challenger Murcia | 2021/09/30 15:00 | Ortega-Olmedo, Roberto v Mathias Bourgue | 6-7,4-6 |
| Challenger Murcia | 2021/09/27 17:05 | Vanneste, Jeroen v Ortega-Olmedo, Roberto | 4-6,6-3,3-6 |
| Challenger Braga | 2021/09/20 11:30 | Cacao, Tiago v Ortega-Olmedo, Roberto | 4-6,6-1,6-1 |
| ITF M25 Madrid | 2021/09/16 09:15 | Ortega-Olmedo, Roberto v Luca Nardi | 4-6,2-6 |
| ITF M25 Madrid | 2021/09/14 09:10 | Ortega-Olmedo, Roberto v Ignacio Monzon | 6-3,6-2 |
| Challenger Seville | 2021/09/06 19:00 | Ortega-Olmedo, Roberto v Adrian Andreev | 6-7,0-6 |
| Challenger Mallorca | 2021/09/02 14:30 | Joao Sousa v Ortega-Olmedo, Roberto | 6-3,6-3 |
| ITF - M25 Loulé | 2021/10/13 14:05 | Yusuke Takahashi v Alberto Barroso Campos | 2-6,6-1,6-4 |
| ITF M25 Setubal | 2021/10/08 12:15 | Yusuke Takahashi v Laurent Lokoli | 2-6,6-2,0-6 |
| ITF M25 Setubal | 2021/10/07 13:55 | Yusuke Takahashi v Alberto Barroso Campos | 6-4,6-3 |
| ITF M25 Setubal | 2021/10/06 10:00 | Mukund Sasikumar v Yusuke Takahashi | 3-6,3-6 |
| ITF M25 Falun | 2021/09/29 11:00 | Yusuke Takahashi v Khumoyun Sultanov | 2-6,0-6 |
| ITF M25 Falun | 2021/09/27 12:00 | Dembek, Michal v Yusuke Takahashi | 6-7,6-2,3-6 |
| Challenger Columbus | 2021/09/19 14:00 | Gijs Brouwer v Yusuke Takahashi | 6-1,7-6 |
| ITF M25 Decatur | 2021/08/05 15:00 | Yusuke Takahashi v Gijs Brouwer | 1-6,0-6 |