Stadium: Court 5 Round: 1
| LTA British Tour | 2020/07/18 17:35 | Marcus Walters v Gray, Jonathan | 6-7,4-6 |
| LTA British Tour | 2020/07/18 13:10 | Daniel Little v Gray, Jonathan | 6-4,4-6,5-10 |
| UK Tennis Series | 2020/07/12 13:00 | Hands, Tom v Gray, Jonathan | 6-4,6-4 |
| UK Tennis Series | 2020/07/11 09:00 | Glasspool, Lloyd v Gray, Jonathan | 6-4,6-3 |
| 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 | 2020/07/18 17:20 | Joe Tyler v Carr, Simon | 1-6,2-6 |
| LTA British Tour | 2020/07/18 13:15 | Meehan, Harry David v Carr, Simon | 1-6,3-6 |
| Challenger Potchefstroom | 2020/03/10 11:05 | Lorenzo Musetti v Carr, Simon | 6-2,7-5 |
| Potchefstroom, Singles Qualifying M-ITF-RSA-01A | 2020/03/03 09:30 | Carr, Simon v Simon, Tobias | 7-6,6-7,3-6 |
| ATP - Dubaï | 2020/02/22 07:00 | Yannick Hanfmann v Carr, Simon | 7-6,6-1 |
| ITF M15 Cancun | 2020/02/06 16:50 | Felix Corwin v Carr, Simon | 6-3,7-5 |
| ITF M15 Cancun | 2020/02/05 20:00 | Boyer, Dusty H v Carr, Simon | 6-7,2-6 |
| ITF M15 Cancun | 2020/01/28 15:30 | Kirkov, Vasil v Carr, Simon | 6-4,7-5 |