| UK Pro League | 2021/03/02 16:15 | Gray, Jonathan v Weightman, Oscar | 6-3,6-2 |
| UK Pro League | 2021/03/16 12:30 | Gray, Jonathan v Sean Hodkin | 6-4,4-6,8-10 |
| UK Pro League | 2021/03/15 10:00 | Gray, Jonathan v Harry Wendelken | 7-6,6-3 |
| 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 |
| 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 | 2021/03/02 16:15 | Gray, Jonathan v Weightman, Oscar | 6-3,6-2 |