Stadium: Court 1 Round: 28 Ground: Clay
| ITF M15 Cairo | 2021/11/25 08:00 | Gray, Jonathan v Nathan Seateun | 7-6,6-4 |
| ITF M15 Cairo | 2021/11/24 11:40 | Gray, Jonathan v El-Moslemany, Omar | 6-2,6-0 |
| ITF M15 Benicarlo | 2021/11/10 12:35 | Gray, Jonathan v Alex M Pujolras | 4-6,6-3,6-7 |
| ITF M15 Benicarlo | 2021/11/09 08:30 | Gray, Jonathan v Gian Marco Ortenzi | 3-6,6-4,10-5 |
| 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 Maxted, Lui | 1-6,3-6 |
| ITF M15 Cairo | 2021/11/26 08:00 | Acquaroli, Gianluca v Edoardo Zanada | 6-1,6-2 |
| ITF M15 Cairo | 2021/11/25 08:00 | Hady Habib v Acquaroli, Gianluca | 6-1,4-6,4-6 |
| ITF M15 Cairo | 2021/11/24 09:20 | Acquaroli, Gianluca v El Feky, Karim | 6-2,6-1 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/09/05 11:40 | Mateus Alves v Acquaroli, Gianluca | 6-7,7-5,6-4 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/09/04 13:55 | Acquaroli, Gianluca v Aziz Ouakaa | 7-6,6-2 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/09/03 09:00 | Coppini, Alessandro v Acquaroli, Gianluca | 4-6,2-6 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/09/02 16:00 | Acquaroli, Gianluca v Mendez, Matthew | 6-2,6-2 |
| Tabarka, Singles Qualifying M-ITF-TUN-41A | 2019/09/01 11:00 | Acquaroli, Gianluca v Caspar Schuetze | 6-3,6-2 |