Stadium: Court 3 Round: 1
| LTA British Tour | 2020/08/22 12:15 | Gray, Jonathan v Daniel Little | 7-5,4-6,12-10 |
| LTA British Tour | 2020/07/18 13:10 | Daniel Little v Gray, Jonathan | 6-4,4-6,5-10 |
| LTA British Tour | 2020/09/04 10:00 | Daniel Little v Hersey, Jake | 6-4,6-2 |
| LTA British Tour | 2020/08/30 11:30 | Anton Matusevich v Daniel Little | 6-4,6-4 |
| LTA British Tour | 2020/08/29 14:10 | Daniel Little v Felix Gill | 6-0,7-5 |
| LTA British Tour | 2020/08/29 10:15 | Daniel Little v Cash, Julian | 6-2,1-6,10-6 |
| LTA British Tour | 2020/08/28 18:50 | Jack Gibbens v Daniel Little | 4-6,3-6 |
| LTA British Tour | 2020/08/22 12:15 | Gray, Jonathan v Daniel Little | 7-5,4-6,12-10 |
| 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 |
| 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 |
| 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 |