Stadium: Court 5 North Round: 25 Ground: Hardcourt indoor
| 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 |
| Challenger Glasgow | 2019/09/17 14:05 | Lloyd Glasspool v Nicola Kuhn | 6-3,4-6,3-6 |
| Challenger Glasgow | 2019/09/16 15:10 | Lloyd Glasspool v Riccardo Balzerani | 6-3,6-2 |
| Challenger Cassis | 2019/09/02 08:30 | Lloyd Glasspool v Illya Marchenko | 4-6,4-6 |
| Challenger Vancouver | 2019/08/15 22:15 | Ricardas Berankis v Lloyd Glasspool | 7-6,6-1 |
| Challenger Vancouver | 2019/08/14 21:30 | Lloyd Glasspool v Taha Baadi | 6-3,6-2 |
| Challenger Vancouver | 2019/08/13 02:05 | Jordi Arconada v Lloyd Glasspool | 5-7,3-6 |
| Challenger Aptos | 2019/08/05 23:00 | Lloyd Glasspool v Martin Redlicki | 6-7,4-6 |
| Challenger Lexington | 2019/08/03 18:00 | Lloyd Glasspool v Alex Bolt | 3-6,2-6 |
| ITF M25 Harlingen | 2019/09/27 22:00 | Govind Nanda v Jonathan Gray | 6-3,4-6,6-2 |
| ITF M25 Harlingen | 2019/09/26 15:00 | Jonathan Gray v Nick Hardt | 6-3,6-4 |
| ITF M25 Harlingen | 2019/09/25 15:30 | Peter Bothwell v Jonathan Gray | 6-3,4-6,4-6 |
| ITF M25 Houston | 2019/09/18 19:00 | Jonathan Gray v Andrew Watson | 2-6,3-6 |
| ITF M15 Jakarta | 2019/08/22 02:30 | Jonathan Gray v Aaron Schmid | 4-6,7-5,2-6 |
| ITF M15 Jakarta | 2019/08/20 06:40 | Jonathan Gray v Jiaqi Duan | 7-6,6-2 |
| ITF M15 Jakarta | 2019/08/14 06:00 | Jonathan Gray v Ruan Roelofse | 6-7,3-6 |
| ITF M15 Jakarta | 2019/08/09 02:30 | Emiliano Maggioli v Jonathan Gray | 6-1,6-2 |