Stadium: Court 4 Round: 25 Ground: Clay
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/23 11:55 | Gray, Jonathan v Louis Tessa | 4-6,3-6 |
| ITF Tunisia F5 | 2015/10/06 08:30 | Gray, Jonathan v Louis Tessa | 4-6,6-7 |
| ITF Tunisia F25 Qual | 2015/09/27 09:00 | Louis Tessa v Gray, Jonathan | 1-6,6-3,2-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/23 11:55 | Gray, Jonathan v Louis Tessa | 4-6,3-6 |
| ITF M15 Madrid | 2019/04/17 11:40 | Benjamin Winter Lopez v Gray, Jonathan | 7-6,6-3 |
| 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 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/26 10:55 | Louis Tessa v Matos, Rafael | 2-6,2-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/25 12:30 | Louis Tessa v Jirousek, Tomas | 6-3,6-4 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/04/23 11:55 | Gray, Jonathan v Louis Tessa | 4-6,3-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/03/23 14:15 | Louis Tessa v Vit Kopriva | 4-6,0-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/03/23 10:00 | Arthur Rinderknech v Louis Tessa | 4-6,6-3,5-10 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/03/22 14:30 | Arthur Rinderknech v Louis Tessa | 4-6,6-3,0-1 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/03/19 12:50 | Juan Pablo Paz v Louis Tessa | 4-6,6-2,5-7 |
| ITF - M15 Monastir | 2019/02/08 08:30 | Louis Tessa v Hoyt, Evan | 2-6,2-6 |