Round: 1
| Houston, Singles Qualifying M-ITF-USA-28A | 2019/09/18 19:00 | Gray, Jonathan v Watson, Andrew | 2-6,3-6 |
| UK Pro League | 2021/03/05 11:15 | Recci, Mason v Gray, Jonathan | 7-5,6-4 |
| UK Pro League | 2021/03/04 17:00 | Gray, Jonathan v Findel-Hawkins, Jack | 4-6,3-6 |
| UK Pro League | 2021/03/03 12:30 | Anton Matusevich v Gray, Jonathan | 6-3,6-4 |
| UK Pro League | 2021/03/02 16:15 | Gray, Jonathan v Weightman, Oscar | 6-3,6-2 |
| UK Pro League | 2021/03/01 10:00 | Gray, Jonathan v Paris, Joshua | 3-6,6-7 |
| LTA British Tour | 2020/09/06 09:00 | Arthur Fery v Gray, Jonathan | 6-4,3-6,10-8 |
| LTA British Tour | 2020/09/05 12:05 | Gray, Jonathan v Alexis Canter | 7-5,6-2 |
| LTA British Tour | 2020/09/05 09:00 | Daniel Little v Gray, Jonathan | 6-7,3-6 |
| UK Pro League | 2021/03/05 14:00 | Billy Harris v Watson, Andrew | 6-2,6-1 |
| UK Pro League | 2021/03/04 10:00 | Watson, Andrew v Daniel Cox | 0-6,0-6 |
| UK Pro League | 2021/03/03 15:30 | Mark Whitehouse v Watson, Andrew | 7-6,6-2 |
| UK Pro League | 2021/03/02 12:30 | Watson, Andrew v Sean Hodkin | 2-6,3-6 |
| UK Pro League | 2021/03/01 14:00 | Watson, Andrew v George Houghton | 1-6,2-6 |
| ITF M25 Norman | 2019/10/01 17:20 | Watson, Andrew v Strong Kirchheimer | 3-6,1-6 |
| ITF M25 Harlingen | 2019/09/27 00:30 | Adrian Andreev v Watson, Andrew | 6-4,6-3 |
| ITF M25 Harlingen | 2019/09/26 02:55 | Khan, Zane v Watson, Andrew | 4-6,1-6 |