Stadium: Court 2 Round: 166 Ground: Clay
| ITF M25 Most | 2019/05/29 08:00 | Simon, Tobias v Recek, Dominik | 5-7,4-6 |
| Samarkand, Uzbekistan | 2019/05/13 11:20 | Zhurbin, Alexander v Simon, Tobias | 7-6,6-7,7-5 |
| Shymkent 2, Kazakhstan | 2019/05/09 10:45 | Simon, Tobias v Jay Clarke | 2-6,7-5,6-7 |
| Shymkent 2, Kazakhstan | 2019/05/07 08:10 | Viktor Durasovic v Simon, Tobias | 6-7,5-7 |
| Shymkent 2, Kazakhstan | 2019/05/06 05:40 | Simon, Tobias v Gijs Brouwer | 3-6,6-4,7-5 |
| Challenger Bordeaux | 2019/04/29 08:00 | Simon, Tobias v Hugo Nys | 2-6,4-6 |
| ITF - M25 Angers | 2019/04/26 13:20 | Simon, Tobias v Nikolas Sanchez Izquierdo | 6-2,5-7,2-6 |
| ITF - M25 Angers | 2019/04/25 16:10 | Simon, Tobias v Christoph Negritu | 6-4,6-7,6-0 |
| Challenger Vicenza | 2019/05/28 09:30 | Benjamin Hassan v Jacopo Berrettini | 6-4,6-7,6-3 |
| ITF M25 Vic | 2019/05/25 09:00 | Jacopo Berrettini v Raul Brancaccio | 5-7,3-6 |
| ITF M25 Vic | 2019/05/23 12:25 | Jacopo Berrettini v Alexander Weis | 6-4,6-0 |
| ITF M25 Vic | 2019/05/22 13:30 | Jacopo Berrettini v Felipe Meligeni Rodrigues Alves | 6-4,6-2 |
| Rome, Italy | 2019/05/11 15:25 | Taylor Fritz v Jacopo Berrettini | 6-4,6-3 |
| Challenger Francavilla | 2019/04/22 11:20 | Riccardo Bonadio v Jacopo Berrettini | 7-5,3-6,6-3 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/18 12:00 | Hamou, Maxime v Jacopo Berrettini | 6-4,6-2 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/17 10:10 | Simon Freund v Jacopo Berrettini | 3-6,3-6 |