Stadium: COURT 8 Round: 26 Ground: Hardcourt outdoor
| ITF M25 Johannesburg | 2021/09/14 08:00 | Konstantin Kravchuk v Alastair Gray | 4-6,3-6 |
| ITF M25 Sintra | 2021/09/08 09:00 | Paul Jubb v Alastair Gray | 6-4,6-4 |
| ITF M25 Sintra | 2021/09/07 10:45 | Alastair Gray v Henrik Heise Korsgaard | 6-1,6-4 |
| ITF M25 Sintra | 2021/09/06 12:00 | Alastair Gray v Mirko Lagasio | 6-0,6-2 |
| ITF M25 Bagneres-De-Bigorre | 2021/09/02 12:00 | Alastair Gray v Arthur Fils | 3-6,6-4,4-6 |
| ITF M25 Bagneres-De-Bigorre | 2021/09/01 13:45 | Harold Mayot v Alastair Gray | 2-6,7-5,4-6 |
| ATP Eastbourne | 2021/06/22 12:30 | Alastair Gray v Ilya Ivashka | 2-6,6-7 |
| ATP Eastbourne | 2021/06/20 11:10 | Alastair Gray v James Duckworth | 3-6,6-7 |
| ITF M25 Johannesburg | 2021/09/15 12:00 | Ethan D Sibanda v Vasilios Caripi | 4-6,6-4,0-6 |
| ITF M25 Johannesburg | 2021/09/13 13:30 | Omer Yeshaya v Vasilios Caripi | 1-6,6-7 |
| ITF M25 Johannesburg | 2021/09/13 08:30 | James Edley v Vasilios Caripi | 6-4,6-7,4-10 |
| ITF M25 Johannesburg | 2021/09/12 10:40 | Lwazi Ngwenya v Vasilios Caripi | 4-6,4-6 |
| ITF M25 Wetzlar | 2021/08/02 10:00 | Vasilios Caripi v Lorenzo Joaquin Rodriguez | 0-6,1-6 |
| ITF M15 Heraklion | 2021/06/06 09:00 | Vasilios Caripi v Matteo De Vincentis | 2-6,2-6 |
| ITF M15 Heraklion | 2021/05/30 09:00 | Rishab Agarwal v Vasilios Caripi | 6-1,6-4 |
| ITF M15 Heraklion | 2021/05/23 10:00 | Gianmarco Ferrari v Vasilios Caripi | 6-3,6-0 |