| ITF M15 Heraklion | 2020/02/19 15:35 | Jonathan Gray v Alexander Shevchenko | 4-6,7-6,3-6 |
| ITF M15 Heraklion | 2020/02/12 14:15 | Lodewijk Weststrate v Jonathan Gray | 7-5,6-3 |
| ITF M15 Manacor | 2020/01/14 11:00 | Abedallah Shelbayh v Jonathan Gray | 7-6,2-6,6-1 |
| ITF M15 Manacor | 2020/01/09 10:50 | Jonathan Gray v Pawel Juszczak | 3-6,4-6 |
| ITF M15 Manacor | 2020/01/08 08:55 | Jonathan Gray v Abedallah Shelbayh | 6-2,5-7,7-5 |
| ITF M25 Fort Worth | 2019/10/22 18:30 | Liam Broady v Jonathan Gray | 6-0,6-2 |
| ITF M25 Waco | 2019/10/16 18:00 | Alex Rybakov v Jonathan Gray | 6-1,7-5 |
| ITF M25 Claremont | 2019/10/09 18:40 | Connor Farren v Jonathan Gray | 3-6,6-3,6-4 |
| 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 |