Estadio: Pista 4 Round: 25 Ground: Hardcourt outdoor
| Challenger de Segovia | 2019/08/01 14:05 | Constant Lestienne v Tobias Simon | 7-6,6-2 |
| Challenger de Segovia | 2019/07/30 08:00 | Tobias Simon v Aldin Setkic | 7-5,6-4 |
| Challenger de Segovia | 2019/07/29 08:00 | Botic Van De Zandschulp v Tobias Simon | 5-7,5-7 |
| Challenger de Granby | 2019/07/23 15:40 | Joshua Peck v Tobias Simon | 6-4,6-4 |
| ITF M25 Bakio | 2019/07/02 13:55 | Sergi Perez Contri v Tobias Simon | 6-3,6-2 |
| ITF M25 Arlon | 2019/06/25 16:50 | Tobias Simon v Zizou Bergs | 5-7,5-7 |
| Challenger de Bratislava | 2019/06/17 15:20 | Jeremy Jahn v Tobias Simon | 6-4,6-7,6-1 |
| ITF M25 Huelva | 2019/06/14 15:00 | Tobias Simon v Pol Martin Tiffon | 4-6,4-6 |
| ITF M25 Pozoblanco | 2019/08/06 07:30 | Juan P. Cañas García v Daniel Salazar | 7-6,6-3 |
| ITF M15 Játiva | 2019/07/31 14:00 | Juan P. Cañas García v Carlos Lopez Montagud | 1-6,3-6 |
| ITF M15 Tanger | 2019/07/17 11:35 | Adam Moundir v Juan P. Cañas García | 6-4,6-2 |
| ITF M15 Idanha-a-Nova | 2019/07/10 09:00 | Aidan Mchugh v Juan P. Cañas García | 6-2,6-4 |
| ITF M15 Idanha-a-Nova | 2019/07/09 09:00 | Juan P. Cañas García v Terence Das | 6-4,6-4 |
| ITF M15 Idanha-a-Nova | 2019/07/08 09:00 | Juan P. Cañas García v Paulo Fernandes | 7-5,6-3 |
| ITF M15 Idanha-a-Nova | 2019/07/04 10:50 | Fred Gil v Juan P. Cañas García | 6-1,6-3 |
| ITF M15 Idanha-a-Nova | 2019/07/03 11:20 | Francisco Cabral v Juan P. Cañas García | 3-6,2-6 |