Stadium: Pista 3 Round: 26 Ground: Hardcourt outdoor
| ITF M25 - Pozoblanco | 2019/08/07 17:15 | Tobias Simon v Juan P Canas Garcia | 7-5,6-2 |
| Challenger Segovia | 2019/08/01 14:05 | Constant Lestienne v Tobias Simon | 7-6,6-2 |
| Challenger Segovia | 2019/07/30 08:00 | Tobias Simon v Aldin Setkic | 7-5,6-4 |
| Challenger Segovia | 2019/07/29 08:00 | Botic Van De Zandschulp v Tobias Simon | 5-7,5-7 |
| Challenger 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 Bratislava | 2019/06/17 15:20 | Jeremy Jahn v Tobias Simon | 6-4,6-7,6-1 |
| ITF M25 - Pozoblanco | 2019/08/07 16:00 | Rayane Roumane v Benjamin Winter Lopez | 6-0,6-3 |
| ITF M25 - Roehampton | 2019/07/31 13:55 | Rayane Roumane v Alastair Gray | 1-6,4-6 |
| ITF M25 - Roehampton | 2019/07/31 08:30 | Rayane Roumane v George Houghton | 6-2,7-6 |
| ITF M25 - Porto | 2019/07/26 14:30 | Rayane Roumane v Antoine Cornut-Chauvinc | 0-6,3-6 |
| ITF M25 - Porto | 2019/07/25 20:05 | Rayane Roumane v Peter Goldsteiner | 6-3,6-0 |
| ITF M25 - Porto | 2019/07/24 15:30 | Rayane Roumane v Piotr Matuszewski | 6-7,7-6,6-1 |
| ITF M15 - Castelo Branco | 2019/07/19 09:00 | Rayane Roumane v Nuno Borges | 7-5,4-6,3-6 |
| ITF M15 - Castelo Branco | 2019/07/18 12:45 | Rayane Roumane v Andrej Glvac | 7-5,6-4 |