Stadium: Court 5 Round: 1
| ITF M25 Sunderland | 2020/02/25 10:00 | Jesper De Jong v Daniel Little | 6-7,7-5,6-3 |
| ITF M25 Barnstaple | 2020/02/12 13:05 | Jan Zielinski v Daniel Little | 6-3,6-4 |
| ITF M25 Barnstaple | 2020/02/11 12:10 | Daniel Little v Evan Hoyt | 7-6,7-6 |
| ITF M25 Barnstaple | 2020/02/09 10:00 | David Quayle v Daniel Little | 2-6,2-6 |
| ITF M25 Shrewsbury | 2019/09/23 13:15 | Daniel Little v Josip Krstanovic | 4-6,4-6 |
| ITF M25 Shrewsbury | 2019/09/23 08:30 | Daniel Little v Joshua Golding | 4-6,6-3,10-4 |
| ITF M25 Chiswick | 2019/08/05 18:40 | Alexis Canter v Daniel Little | 7-6,6-2 |
| ITF M25 Chiswick | 2019/08/05 12:40 | Daniel Little v Edward Hubner | 6-2,6-1 |
| UK Tennis Series | 2020/07/12 13:00 | Tom Hands v Jonathan Gray | 6-4,6-4 |
| UK Tennis Series | 2020/07/11 09:00 | Lloyd Glasspool v Jonathan Gray | 6-4,6-3 |
| UK Tennis Series | 2020/07/10 11:30 | Jonathan Gray v Julian Cash | 3-6,7-6,3-10 |
| UK Tennis Series | 2020/07/09 15:30 | Ryan James Storrie v Jonathan Gray | 3-6,6-2,10-7 |
| UK Tennis Series | 2020/07/07 13:00 | Mark Whitehouse v Jonathan Gray | 6-3,6-4 |
| UK Tennis Series | 2020/07/06 09:00 | Alexis Canter v Jonathan Gray | 3-0 |
| LTA British Tour | 2020/07/04 09:00 | Arthur Fery v Jonathan Gray | 6-2,6-1 |
| LTA British Tour | 2020/07/03 13:00 | Jonathan Gray v Anton Matusevich | 6-4,3-6,10-8 |