| LTA British Tour | 09/06 09:00 | 1 | Arthur Fery v Jonathan Gray | 6-4,3-6,10-8 | |
| LTA British Tour | 09/05 12:05 | - | Jonathan Gray v Alexis Canter | 7-5,6-2 | |
| LTA British Tour | 09/05 09:00 | 1 | Daniel Little v Jonathan Gray | 6-7,3-6 | |
| LTA British Tour | 09/04 10:00 | 1 | Yujiro Onuma v Jonathan Gray | 3-6,3-6 | |
| LTA British Tour | 08/28 19:55 | - | Felix Gill v Jonathan Gray | 6-3,7-6 | |
| LTA British Tour | 08/23 09:00 | 1 | Jonathan Gray v Arthur Fery | 2-6,5-7 | |
| LTA British Tour | 08/22 12:15 | 1 | Jonathan Gray v Daniel Little | 7-5,4-6,12-10 | |
| LTA British Tour | 08/22 09:00 | 1 | Jonathan Gray v Brandon Murphy | 2-6,7-5,10-4 | |
| LTA British Tour | 08/21 10:00 | 1 | Jonathan Gray v Alexander Jhun | 7-6,6-0 | |
| UK Tennis Series | 07/22 13:00 | 1 | Jan Choinski v Jonathan Gray | Retired | |
| UK Tennis Series | 07/21 11:30 | 1 | Jonathan Gray v Alexis Canter | 3-6,2-6 | |
| UK Tennis Series | 07/20 11:30 | 1 | Luke Johnson v Jonathan Gray | 6-3,6-7,11-9 |