Estadio: Court 5 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Yakarta | 2019/08/22 02:30 | Jonathan Gray v Aaron Schmid | 4-6,7-5,2-6 |
| ITF M15 Yakarta | 2019/08/20 06:40 | Jonathan Gray v Jiaqi Duan | 7-6,6-2 |
| ITF M15 Yakarta | 2019/08/14 06:00 | Jonathan Gray v Ruan Roelofse | 6-7,3-6 |
| ITF M15 Yakarta | 2019/08/09 02:30 | Emiliano Maggioli v Jonathan Gray | 6-1,6-2 |
| ITF M15 Yakarta | 2019/08/08 02:30 | Jonathan Gray v Chien Hsun Lo | 6-2,6-0 |
| ITF M15 Yakarta | 2019/08/07 02:30 | Jonathan Gray v Justin Barki | 7-5,6-3 |
| ITF M15 Idanha-a-Nova | 2019/07/13 09:30 | David Jorda Sanchis v Jonathan Gray | 7-6,6-2 |
| ITF M15 Idanha-a-Nova | 2019/07/12 09:00 | Francisco Dias v Jonathan Gray | 2-6,4-6 |
| ITF M15 Champaign | 2019/09/12 19:30 | Liam Draxl v Andrew Watson | 6-2,7-5 |
| ITF M15 Champaign | 2019/09/10 18:00 | Grey Hamilton v Andrew Watson | 1-6,1-6 |
| ITF M25 Chiswick | 2019/08/06 12:55 | Andrew Watson v Anton Matusevich | 4-6,6-2,4-6 |
| ITF M25 Dublín | 2019/08/03 11:55 | Andrew Watson v Ryan Peniston | 4-6,6-2,4-6 |
| ITF M25 Dublín | 2019/08/02 11:30 | Andrew Watson v Jack Findel-Hawkins | 4-6,6-4,6-4 |
| ITF M25 Dublín | 2019/08/01 15:00 | Andrew Watson v Joe Tyler | 6-4,6-2 |
| ITF M25 Dublín | 2019/07/31 10:05 | Andrew Watson v Osgar O'Hoisin | 7-5,6-4 |
| ITF M15 Idanha-a-Nova | 2019/07/09 09:00 | David Jorda Sanchis v Andrew Watson | 5-7,7-6,6-1 |