| ITF M25 Norman | 2019/10/01 16:30 | Glasspool, Lloyd v Gray, Jonathan | 3-6,2-6 |
| ITF Great Britain F3 | 2018/02/13 15:15 | Glasspool, Lloyd v Gray, Jonathan | 7-6,6-1 |
| ITF Great Britain F5 | 2017/09/20 08:30 | Glasspool, Lloyd v Gray, Jonathan | 2-6,6-4,6-2 |
| UK Tennis Series | 2020/07/10 14:15 | Glasspool, Lloyd v Johnson, Luke | 4-6,3-6 |
| UK Tennis Series | 2020/07/09 09:00 | Glasspool, Lloyd v Willis, Marcus | 6-4,6-2 |
| UK Tennis Series | 2020/07/08 13:00 | Hands, Tom v Glasspool, Lloyd | 6-3,4-6,2-10 |
| UK Tennis Series | 2020/07/07 09:00 | Glasspool, Lloyd v Billy Harris | 1-6,5-7 |
| UK Tennis Series | 2020/07/06 15:00 | Glasspool, Lloyd v Toby Martin | 6-3,6-3 |
| LTA British Tour | 2020/07/04 09:00 | Glasspool, Lloyd v Billy Harris | 4-6,3-6 |
| LTA British Tour | 2020/07/03 11:30 | Glasspool, Lloyd v Paris, Joshua | 6-3,6-4 |
| Challenger Columbus | 2020/02/26 18:25 | Nam, Ji Sung v Glasspool, Lloyd | 6-3,6-2 |
| UK Tennis Series | 2020/07/10 11:30 | Gray, Jonathan v Cash, Julian | 3-6,7-6,3-10 |
| UK Tennis Series | 2020/07/09 15:30 | Ryan James Storrie v Gray, Jonathan | 3-6,6-2,10-7 |
| UK Tennis Series | 2020/07/07 13:00 | Mark Whitehouse v Gray, Jonathan | 6-3,6-4 |
| UK Tennis Series | 2020/07/06 09:00 | Alexis Canter v Gray, Jonathan | 3-0 |
| LTA British Tour | 2020/07/04 09:00 | Arthur Fery v Gray, Jonathan | 6-2,6-1 |
| LTA British Tour | 2020/07/03 13:00 | Gray, Jonathan v Anton Matusevich | 6-4,3-6,10-8 |
| ITF - M15 Héraklion | 2020/02/19 15:35 | Gray, Jonathan v Alexander Shevchenko | 4-6,7-6,3-6 |
| ITF - M15 Héraklion | 2020/02/12 14:15 | Lodewijk Weststrate v Gray, Jonathan | 7-5,6-3 |