| UK Pro League | 2021/03/07 18:00 | Gray, Jonathan v Sean Hodkin | 6-7,2-6 |
| 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 |
| 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 Khotkov, Oleg | 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 |