Stadium: Court 2 Round: 62 Ground: Clay
| ITF M15 Benicarlo | 2021/11/08 10:00 | Gray, Jonathan v Jordi Garcia Mestre | 6-1,6-4 |
| ITF M15 Benicarlo | 2021/11/07 14:30 | Gray, Jonathan v Stepanian, Areg | 6-3,6-3 |
| 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 |
| ITF M15 Benicarlo | 2021/11/08 10:00 | Jay Friend v Gian Marco Ortenzi | 0-6,3-6 |
| ITF M15 Benicarlo | 2021/11/07 11:00 | Thijmen Loof v Gian Marco Ortenzi | 2-6,7-6,8-10 |
| ITF - M15 Antalya | 2021/10/19 09:20 | Dan Alexandru Tomescu v Gian Marco Ortenzi | 5-7,7-6,11-9 |
| ITF - M15 Antalya | 2021/10/18 12:00 | Vitek Horak v Gian Marco Ortenzi | 6-4,3-6,7-10 |
| ITF - M15 Antalya | 2021/10/17 07:00 | Dadabaev, Aziz v Gian Marco Ortenzi | 2-6,3-6 |
| ITF - M15 Antalya | 2021/10/12 11:05 | Gian Marco Ortenzi v Yunis, Facundo | 5-7,6-7 |
| ITF - M15 Antalya | 2021/10/11 09:00 | Gian Marco Ortenzi v Habsuda, Simon | 6-4,6-0 |
| ITF M15 Cairo | 2021/09/30 10:20 | Roncalli, Simone v Gian Marco Ortenzi | 2-6,6-3,6-0 |