Stadium: Court 2 Round: 25 Ground: Clay
| Challenger Poznan | 2019/06/03 08:00 | Tobias Simon v Jacopo Berrettini | 2-6,4-6 |
| ITF M25 - Most | 2019/05/29 08:00 | Tobias Simon v Dominik Recek | 5-7,4-6 |
| Challenger Samarkand | 2019/05/13 11:20 | Alexander Zhurbin v Tobias Simon | 7-6,6-7,7-5 |
| Challenger Shymkent | 2019/05/09 10:45 | Tobias Simon v Jay Clarke | 2-6,7-5,6-7 |
| Challenger Shymkent | 2019/05/07 08:10 | Viktor Durasovic v Tobias Simon | 6-7,5-7 |
| Challenger Shymkent | 2019/05/06 05:40 | Tobias Simon v Gijs Brouwer | 3-6,6-4,7-5 |
| Challenger Bordeaux | 2019/04/29 08:00 | Tobias Simon v Hugo Nys | 2-6,4-6 |
| ITF M25 - Angers | 2019/04/26 13:20 | Tobias Simon v Nikolas Sanchez Izquierdo | 6-2,5-7,2-6 |
| ITF M15 - Majadahonda | 2019/05/28 09:00 | Albert Roglan v Tiago Cacao | 6-4,6-3 |
| ITF M25 - Vic | 2019/05/21 12:40 | Eduard Esteve Lobato v Tiago Cacao | 7-5,6-7,6-1 |
| Challenger Lissabon | 2019/05/14 12:30 | Enrique Lopez-Perez v Tiago Cacao | 7-6,6-4 |
| Challenger Lissabon | 2019/05/13 11:00 | Tiago Cacao v Facundo Arguello | 2-6,6-2,6-1 |
| Challenger - Braga | 2019/05/08 14:40 | Jurgen Zopp v Tiago Cacao | 7-5,6-2 |
| Challenger - Braga | 2019/05/06 14:30 | Tiago Cacao v Francisco Cabral | 6-2,6-2 |
| ITF M15 - Madrid | 2019/04/16 11:25 | Felipe Meligeni Rodrigues Alves v Tiago Cacao | 6-2,6-4 |
| ITF M15 - Reus | 2019/04/09 09:50 | Tiago Cacao v Hugo Gaston | 0-6,6-3,3-6 |