Stadium: Pista 3 Round: 26 Ground: Hardcourt outdoor
| Pozoblanco, Singles Qualifying M-ITF-ESP-24A | 2019/08/07 17:15 | Simon, Tobias v Canas Garcia, Juan Pablo | 7-5,6-2 |
| Segovia, Spain | 2019/08/01 14:05 | Constant Lestienne v Simon, Tobias | 7-6,6-2 |
| Segovia, Spain | 2019/07/30 08:00 | Simon, Tobias v Aldin Setkic | 7-5,6-4 |
| Segovia, Spain | 2019/07/29 08:00 | Botic Van De Zandschulp v Simon, Tobias | 5-7,5-7 |
| Challenger Granby | 2019/07/23 15:40 | Peck, Joshua v Simon, Tobias | 6-4,6-4 |
| ITF M25 Bakio | 2019/07/02 13:55 | Sergi Perez Contri v Simon, Tobias | 6-3,6-2 |
| ITF M25 Arlon | 2019/06/25 16:50 | Simon, Tobias v Zizou Bergs | 5-7,5-7 |
| Challenger Bratislava | 2019/06/17 15:20 | Jahn, Jeremy v Simon, Tobias | 6-4,6-7,6-1 |
| Pozoblanco, Singles Qualifying M-ITF-ESP-24A | 2019/08/07 16:00 | Roumane, Rayane v Benjamin Winter Lopez | 6-0,6-3 |
| ITF M25 Roehampton | 2019/07/31 13:55 | Roumane, Rayane v Alastair Gray | 1-6,4-6 |
| ITF M25 Roehampton | 2019/07/31 08:30 | Roumane, Rayane v George Houghton | 6-2,7-6 |
| ITF M25 Porto | 2019/07/26 14:30 | Roumane, Rayane v Cornut-Chauvinc, Antoine | 0-6,3-6 |
| ITF M25 Porto | 2019/07/25 20:05 | Roumane, Rayane v Goldsteiner, Peter | 6-3,6-0 |
| ITF M25 Porto | 2019/07/24 15:30 | Roumane, Rayane v Matuszewski, Piotr | 6-7,7-6,6-1 |
| ITF M15 Castelo Branco | 2019/07/19 09:00 | Roumane, Rayane v Nuno Borges | 7-5,4-6,3-6 |
| ITF M15 Castelo Branco | 2019/07/18 12:45 | Roumane, Rayane v Glvac, Andrej | 7-5,6-4 |