Stadium: Court 4 Round: 27 Ground: Hardcourt outdoor
| ITF M25 Johannesburg | 2021/09/16 10:00 | Alastair Gray v Vasilios Caripi | 6-0,6-1 |
| 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 |
| ITF M25 Johannesburg | 2021/09/16 08:00 | Francesco Vilardo v Alafia Ayeni | 3-6,6-1,2-6 |
| ITF M25 Johannesburg | 2021/09/15 08:00 | Alafia Ayeni v Ryan Nijboer | 7-5,6-3 |
| ITF M15 Castelo Branco | 2021/07/27 12:00 | Alafia Ayeni v Joao Lucas Reis da Silva | 4-6,4-6 |
| ITF M25 Idanha-A-Nova | 2021/07/23 09:00 | Simon Carr v Alafia Ayeni | 6-2,6-4 |
| ITF M25 Idanha-A-Nova | 2021/07/22 09:55 | Alafia Ayeni v Tiago Cacao | 7-6,6-4 |
| ITF M25 Idanha-A-Nova | 2021/07/21 09:50 | Alafia Ayeni v Luca Giacomini | 6-1,1-6,6-2 |
| ITF M25 Nur-Sultan | 2021/07/07 04:00 | Alafia Ayeni v Jason Kubler | 2-6,0-6 |
| ITF M25 Nur-Sultan | 2021/07/06 07:45 | Alafia Ayeni v Arystanbek Kaparov | 6-2,6-0 |