Stadium: Court 1 Round: 62 Ground: Clay
| ITF - M15 Torello | 2021/11/02 11:00 | Gray, Jonathan v Wojcik, Yann | 4-6,4-6 |
| UK Pro League | 2021/04/05 11:30 | Gray, Jonathan v Lui Maxted | 1-6,3-6 |
| UK Pro League | 2021/03/21 12:00 | Cash, Julian v Gray, Jonathan | 6-1,6-2 |
| UK Pro League | 2021/03/20 10:45 | Gray, Jonathan v Hands, Tom | 6-4,6-4 |
| UK Pro League | 2021/03/19 12:30 | Gray, Jonathan v Findel-Hawkins, Jack | 3-6,5-7 |
| UK Pro League | 2021/03/18 17:00 | Mark Whitehouse v Gray, Jonathan | 6-0,7-6 |
| UK Pro League | 2021/03/17 10:00 | Gray, Jonathan v Weightman, Oscar | 6-2,6-4 |
| UK Pro League | 2021/03/16 12:30 | Gray, Jonathan v Sean Hodkin | 6-4,4-6,8-10 |
| ITF - M15 Torello | 2021/10/31 13:30 | Ktiri, Marc Othman v Stepanian, Areg | 6-2,7-5 |
| ITF M25 Madrid | 2021/10/24 09:30 | Noah Lopez v Stepanian, Areg | 6-3,6-1 |
| ITF M15 Girona | 2021/10/18 08:00 | Stepanian, Areg v Ivanov, Vladislav | 1-6,3-6 |
| ITF M15 Platja D'Aro | 2021/10/03 08:00 | Stepanian, Areg v Deleersnyder, Clement | 0-6,0-6 |
| ITF - M15 Monastir | 2021/08/25 07:30 | Sadaoui, Mehdi v Stepanian, Areg | 6-0,6-2 |
| ITF M15 Xativa | 2021/08/01 10:00 | Vittar, Francisco v Stepanian, Areg | 6-1,6-0 |
| ITF M25 Denia | 2021/07/25 08:00 | Vrzesinski, Robertas v Stepanian, Areg | 6-0,6-3 |
| ITF - M15 Monastir | 2021/07/04 08:00 | Stepanian, Areg v Jacob Brumm | 2-6,0-6 |