Estadio: Pista 3 Round: 25 Ground: Clay
| Challenger de Mallorca | 2021/09/02 14:30 | Joao Sousa v Roberto Ortega-Olmedo | 6-3,6-3 |
| Challenger de Mallorca | 2021/08/31 10:00 | Roberto Ortega-Olmedo v Nicolas Mejia | 7-5,7-5 |
| Challenger de Praga | 2021/08/23 10:00 | Roberto Ortega-Olmedo v Alexander Ritschard | 1-6,1-6 |
| ITF M25 Frankfurt am Main | 2021/08/11 09:00 | Roberto Ortega-Olmedo v Matthew Romios | 2-6,4-6 |
| Challenger de Segovia | 2021/07/27 14:00 | Roberto Ortega-Olmedo v Cem Ilkel | 6-3,6-7,4-6 |
| Challenger de Pozoblanco | 2021/07/20 17:10 | Tim Van Rijthoven v Roberto Ortega-Olmedo | 6-3,6-7,7-5 |
| Challenger de Iasi | 2021/07/13 10:50 | Matija Pecotic v Roberto Ortega-Olmedo | 4-6,6-0,6-1 |
| ITF M25 Ajaccio | 2021/07/08 17:05 | Clement Chidekh v Roberto Ortega-Olmedo | 6-2,2-6,6-2 |
| Challenger de Luedenscheid | 2021/08/15 11:00 | Matteo Martineau v Adrian Andreev | 6-4,7-5 |
| Challenger de Praga | 2021/08/10 11:45 | Adrian Andreev v Nino Serdarusic | 3-6,3-6 |
| Challenger de Praga | 2021/08/09 09:55 | Adrian Andreev v Facundo Diaz Acosta | 2-6,6-4,6-3 |
| Challenger de Praga | 2021/08/08 12:00 | Adrian Andreev v Aldin Setkic | 7-5,6-1 |
| Challenger de Segovia | 2021/07/26 16:30 | Adrian Andreev v Benjamin Bonzi | 7-6,4-6,6-7 |
| Challenger de Pozoblanco | 2021/07/21 15:00 | Adrian Andreev v Gregoire Barrere | 3-6,0-6 |
| Challenger de Pozoblanco | 2021/07/19 19:45 | Adrian Andreev v Blas Ruiz Romero | 6-0,6-0 |
| Challenger de Iasi | 2021/07/14 08:00 | Lucas Miedler v Adrian Andreev | 7-6,6-1 |