| ITF M25 Norman | 2019/10/01 16:30 | Lloyd Glasspool v Jonathan Gray | 3-6,2-6 |
| ITF Great Britain F3 | 2018/02/13 15:15 | Lloyd Glasspool v Jonathan Gray | 7-6,6-1 |
| ITF Great Britain F5 | 2017/09/20 08:30 | Lloyd Glasspool v Jonathan Gray | 2-6,6-4,6-2 |
| UK Tennis Series | 2020/07/10 14:15 | Lloyd Glasspool v Luke Johnson | 4-6,3-6 |
| UK Tennis Series | 2020/07/09 09:00 | Lloyd Glasspool v Marcus Willis | 6-4,6-2 |
| UK Tennis Series | 2020/07/08 13:00 | Tom Hands v Lloyd Glasspool | 6-3,4-6,2-10 |
| UK Tennis Series | 2020/07/07 09:00 | Lloyd Glasspool v Billy Harris | 1-6,5-7 |
| UK Tennis Series | 2020/07/06 15:00 | Lloyd Glasspool v Toby Martin | 6-3,6-3 |
| LTA British Tour | 2020/07/04 09:00 | Lloyd Glasspool v Billy Harris | 4-6,3-6 |
| LTA British Tour | 2020/07/03 11:30 | Lloyd Glasspool v Joshua Paris | 6-3,6-4 |
| Challenger Columbus | 2020/02/26 18:25 | Ji Sung Nam v Lloyd Glasspool | 6-3,6-2 |
| 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 |
| 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 |