| LTA British Tour | 2020/07/18 13:10 | Daniel Little v Gray, Jonathan | 6-4,4-6,5-10 |
| LTA British Tour | 2020/08/22 09:00 | Gray, Jonathan v Murphy, Brandon | 2-6,7-5,10-4 |
| LTA British Tour | 2020/08/21 10:00 | Gray, Jonathan v Jhun, Alexander | 7-6,6-0 |
| UK Tennis Series | 2020/07/21 11:30 | Gray, Jonathan v Alexis Canter | 3-6,2-6 |
| UK Tennis Series | 2020/07/20 11:30 | Johnson, Luke v Gray, Jonathan | 6-3,6-7,11-9 |
| LTA British Tour | 2020/07/19 13:40 | Arthur Fery v Gray, Jonathan | 6-2,2-6,10-6 |
| LTA British Tour | 2020/07/18 17:35 | Marcus Walters v Gray, Jonathan | 6-7,4-6 |
| LTA British Tour | 2020/07/18 13:10 | Daniel Little v Gray, Jonathan | 6-4,4-6,5-10 |
| UK Tennis Series | 2020/07/12 13:00 | Hands, Tom v Gray, Jonathan | 6-4,6-4 |
| LTA British Tour | 2020/08/22 09:00 | Sean Hodkin v Daniel Little | 1-6,3-6 |
| LTA British Tour | 2020/08/21 10:00 | Felix Gill v Daniel Little | 2-6,3-6 |
| UK Tennis Series | 2020/08/08 16:00 | Daniel Little v Sean Hodkin | 5-7,2-6 |
| UK Tennis Series | 2020/08/07 10:15 | Hands, Tom v Daniel Little | 7-6,4-6,9-11 |
| LTA British Tour | 2020/07/24 14:25 | Charles Broom v Daniel Little | 6-3,6-3 |
| LTA British Tour | 2020/07/23 14:45 | Samuel, Toby v Daniel Little | 1-6,5-7 |
| LTA British Tour | 2020/07/18 13:10 | Daniel Little v Gray, Jonathan | 6-4,4-6,5-10 |
| ITF - M25 Sunderland | 2020/02/25 10:00 | Jesper De Jong v Daniel Little | 6-7,7-5,6-3 |