| UK Pro League | 2021/03/01 10:00 | Gray, Jonathan v Paris, Joshua | 3-6,6-7 |
| LTA British Tour | 2020/09/06 09:00 | Arthur Fery v Gray, Jonathan | 6-4,3-6,10-8 |
| LTA British Tour | 2020/09/05 12:05 | Gray, Jonathan v Alexis Canter | 7-5,6-2 |
| LTA British Tour | 2020/09/05 09:00 | Daniel Little v Gray, Jonathan | 6-7,3-6 |
| LTA British Tour | 2020/09/04 10:00 | Onuma, Yujiro v Gray, Jonathan | 3-6,3-6 |
| LTA British Tour | 2020/08/28 19:55 | Felix Gill v Gray, Jonathan | 6-3,7-6 |
| LTA British Tour | 2020/08/23 09:00 | Gray, Jonathan v Arthur Fery | 2-6,5-7 |
| LTA British Tour | 2020/08/22 12:15 | Gray, Jonathan v Daniel Little | 7-5,4-6,12-10 |
| ITF M15 Nur-Sultan | 2021/02/12 06:45 | Weightman, Oscar v Dambrosi, Giacomo | 1-6,2-6 |
| ITF M15 Nur-Sultan | 2021/02/11 06:55 | Weightman, Oscar v Bondarevskiy, Yan | 7-6,6-3 |
| ITF M15 Nur-Sultan | 2021/02/10 04:45 | Niklas-Salminen, Patrick v Weightman, Oscar | 6-4,4-6,2-6 |
| ITF M15 Nur-Sultan | 2021/02/09 06:45 | Tom Schonenberg v Weightman, Oscar | 3-6,6-3,5-10 |
| ITF M15 Nur-Sultan | 2021/02/08 06:00 | Nikita Sidorov v Weightman, Oscar | 2-6,4-6 |
| ITF M15 Nur-Sultan | 2021/02/03 08:00 | Otto Virtanen v Weightman, Oscar | 6-2,6-2 |
| ITF M15 Nur-Sultan | 2021/02/02 04:00 | Dominik Palan v Weightman, Oscar | 6-3,6-7,5-10 |
| ITF M15 Nur-Sultan | 2021/02/01 05:00 | Pozzi, Davide v Weightman, Oscar | 1-6,0-6 |