| UK Pro League | 2021/03/07 18:00 | Jonathan Gray v Sean Hodkin | 6-7,2-6 |
| UK Pro League | 2021/03/05 11:15 | Mason Recci v Jonathan Gray | 7-5,6-4 |
| UK Pro League | 2021/03/04 17:00 | Jonathan Gray v Jack Findel-Hawkins | 4-6,3-6 |
| UK Pro League | 2021/03/03 12:30 | Anton Matusevich v Jonathan Gray | 6-3,6-4 |
| UK Pro League | 2021/03/02 16:15 | Jonathan Gray v Oscar Weightman | 6-3,6-2 |
| UK Pro League | 2021/03/01 10:00 | Jonathan Gray v Joshua Paris | 3-6,6-7 |
| LTA British Tour | 2020/09/06 09:00 | Arthur Fery v Jonathan Gray | 6-4,3-6,10-8 |
| LTA British Tour | 2020/09/05 12:05 | Jonathan Gray v Alexis Canter | 7-5,6-2 |
| ITF - M15 Sharm El Sheikh | 2021/03/02 09:10 | Roman Andres Burruchaga v Harry Wendelken | 6-4,7-6 |
| ITF - M15 Sharm El Sheikh | 2021/03/01 13:00 | Ignacio B Alia v Harry Wendelken | 1-6,1-6 |
| ITF - M15 Sharm El Sheikh | 2021/02/28 15:30 | Harry Wendelken v Oleg Khotkov | 7-5,6-0 |
| ITF - M15 Sharm El Sheikh | 2021/02/21 09:30 | Arvid Nordquist v Harry Wendelken | 6-7,7-5,10-6 |
| ITF - M15 Parnu | 2020/11/05 13:45 | Harry Wendelken v Leandro Riedi | 3-6,1-6 |
| ITF - M15 Parnu | 2020/11/04 13:15 | David Pichler v Harry Wendelken | 4-6,4-6 |
| ITF - M15 Doha | 2019/12/20 12:00 | Harry Wendelken v Aleksandre Bakshi | 5-7,6-4,1-6 |
| ITF - M15 Doha | 2019/12/19 11:40 | Simon Freund v Harry Wendelken | 0-6,2-6 |