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