Stadium: Centre Court Round: 27 Ground: Hardcourt outdoor
| Singapore, Singles Qualifying M-ITF-SGP-01A | 2019/05/30 02:00 | Bourchier, Harry v Jesse Delaney | 6-1,6-0 |
| Singapore, Singles Qualifying M-ITF-SGP-01A | 2019/05/28 02:00 | Bourchier, Harry v Ross, Jesse | 6-1,6-2 |
| Nonthaburi, Singles M-ITF-THA-01A | 2019/05/25 05:15 | Bourchier, Harry v Sekiguchi, Shuichi | 4-6,4-6 |
| Nonthaburi, Singles M-ITF-THA-01A | 2019/05/24 03:00 | Rio Noguchi v Bourchier, Harry | 5-7,2-6 |
| Nonthaburi, Singles M-ITF-THA-01A | 2019/05/21 06:35 | Kasidit Samrej v Bourchier, Harry | 3-6,6-7 |
| Samarkand, Uzbekistan | 2019/05/13 06:30 | Bourchier, Harry v Karim-Mohamed Maamoun | 2-6,6-7 |
| Shymkent 2, Kazakhstan | 2019/05/08 04:00 | Tomas Barrios Vera v Bourchier, Harry | 3-6,6-3,7-6 |
| Shymkent 2, Kazakhstan | 2019/05/06 08:35 | Bourchier, Harry v Antoine Escoffier | 2-6,6-2,7-5 |
| Singapore, Singles Qualifying M-ITF-SGP-01A | 2019/05/29 02:00 | Hobbs, Roy v Gray, Jonathan | 3-6,4-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/05/01 08:30 | Gray, Jonathan v Louis Tessa | 6-2,1-6,2-6 |
| 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 |