Round: 1
| UK Pro League | 2021/03/17 10:00 | Gray, Jonathan v Weightman, Oscar | 6-2,6-4 |
| UK Pro League | 2021/03/16 15:30 | Mark Whitehouse v Weightman, Oscar | 6-3,7-6 |
| UK Pro League | 2021/03/15 12:30 | Findel-Hawkins, Jack v Weightman, Oscar | 4-6,6-7 |
| UK Pro League | 2021/03/07 13:30 | Weightman, Oscar v Hands, Tom | 4-6,6-4,6-10 |
| UK Pro League | 2021/03/06 14:00 | Sean Hodkin v Weightman, Oscar | 6-2,7-6 |
| UK Pro League | 2021/03/05 10:00 | Anton Matusevich v Weightman, Oscar | 6-4,6-4 |
| UK Pro League | 2021/03/04 15:30 | Paris, Joshua v Weightman, Oscar | 6-3,6-4 |
| UK Pro League | 2021/03/03 10:00 | Findel-Hawkins, Jack v Weightman, Oscar | 6-7,6-4,5-10 |
| UK Pro League | 2021/03/17 12:30 | Sean Hodkin v Harry Wendelken | 6-3,3-6,10-8 |
| UK Pro League | 2021/03/16 15:30 | Findel-Hawkins, Jack v Harry Wendelken | 3-6,6-4,5-10 |
| UK Pro League | 2021/03/15 10:00 | Gray, Jonathan v Harry Wendelken | 7-6,6-3 |
| 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 |