Stadium: Court 4 Round: 25 Ground: Hardcourt outdoor
| 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 Idanha-a-Nova | 2019/07/11 13:20 | Ratsaratany, Loic v Gray, Jonathan | 3-6,6-7 |
| ITF M15 Idanha-a-Nova | 2019/07/09 09:00 | Daniel Batista v Gray, Jonathan | 5-7,6-4,1-6 |
| Singapore, Singles Qualifying M-ITF-SGP-01A | 2019/06/16 03:00 | Aidan Mchugh v Gray, Jonathan | 6-2,6-2 |
| Jakarta, Singles Main, M-ITF-INA-02A | 2019/08/08 03:55 | Vladyslav Orlov v Roelofse, Ruan | 7-6,6-2 |
| Jakarta, Singles Main, M-ITF-INA-02A | 2019/08/07 02:30 | Crnokrak, Alexander v Roelofse, Ruan | 4-6,4-6 |
| ITF M25 Champaign | 2019/07/26 20:30 | Oliver Crawford v Roelofse, Ruan | 6-3,6-4 |
| ITF M25 Champaign | 2019/07/25 21:55 | Adamson, Alec v Roelofse, Ruan | 7-6,4-6,5-7 |
| ITF M25 Champaign | 2019/07/24 19:05 | Juan Carlos Aguilar v Roelofse, Ruan | 2-6,5-7 |
| Saarlouis, Singles Qualifying M-ITF-GER-07A | 2019/07/03 10:00 | Gelhardt, Luca v Roelofse, Ruan | 7-5,6-3 |
| Palma Del Rio, Singles M-ITF-ESP-15A | 2019/06/29 20:35 | Roelofse, Ruan v Arthur Rinderknech | 2-6,3-6 |
| Palma Del Rio, Singles M-ITF-ESP-15A | 2019/06/28 20:30 | John Echeverria v Roelofse, Ruan | 6-7,6-4,3-6 |