Stadium: Court 4 Round: 25 Ground: Clay
| ITF M15 Madrid | 2019/04/15 13:30 | Pol Martin Tiffon v Benjamin Winter Lopez | 4-6,5-7 |
| ITF M15 Madrid | 2019/04/15 09:30 | Sergi Perez Contri v Benjamin Winter Lopez | 6-3,4-6,1-10 |
| ITF M15 Reus | 2019/04/08 07:30 | Benjamin Winter Lopez v Ordeig, Roger | 6-4,6-3 |
| Murcia, Singles Qualifying M-ITF-ESP-06A | 2019/03/21 11:50 | Lopez San Martin, Alvaro v Benjamin Winter Lopez | 6-4,7-5 |
| Portimao, Singles Qualifying M-ITF-POR-16A | 2019/03/13 14:15 | Benjamin Winter Lopez v Craig, Henry | 1-6,3-6 |
| Portimao, Singles Qualifying M-ITF-POR-16A | 2019/03/12 11:00 | Benjamin Winter Lopez v Vernier, Michel | 6-3,6-2 |
| Portimao, Singles Qualifying M-ITF-POR-16A | 2019/03/11 10:00 | Petr Nouza v Benjamin Winter Lopez | 3-6,5-7 |
| ITF M15 Loule | 2019/03/07 13:15 | Benjamin Winter Lopez v Lopez San Martin, Alvaro | 5-7,3-6 |
| ITF M15 Madrid | 2019/04/15 16:30 | Gray, Jonathan v Arthur Reymond | 6-3,6-2 |
| ITF M15 Madrid | 2019/04/15 11:00 | Gray, Jonathan v Blanco Damea, Alvaro | 6-3,6-7,13-11 |
| Bolton, Qualifications Simples M-ITF-GBR-03A | 2019/04/02 09:00 | Gray, Jonathan v Gijs Brouwer | 6-7,7-6,4-6 |
| ITF - M25 Calabasas | 2019/03/22 20:00 | Gray, Jonathan v Stefan Kozlov | 2-6,1-6 |
| ITF - M25 Calabasas | 2019/03/22 02:25 | Keegan Smith v Gray, Jonathan | 3-6,7-6,1-6 |
| ITF - M25 Calabasas | 2019/03/20 19:05 | Hahn, Eric v Gray, Jonathan | 2-6,2-6 |
| ITF - M25 Calabasas | 2019/03/19 18:55 | Gray, Jonathan v Griffith, William | 6-2,7-6 |
| ITF - M25 Calabasas | 2019/03/18 17:00 | Evan Zhu v Gray, Jonathan | 3-6,2-6 |