Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| Challenger Eckental | 2021/10/31 13:00 | Uladzimir Ignatik v Benjamin Hassan | 6-3,6-4 |
| Tie Break Tens Dubai | 2021/10/22 15:50 | Gael Monfils v Benjamin Hassan | 0-0 |
| UTR Pro Tennis Series Mulheim | 2021/10/16 08:00 | Benjamin Hassan v Tom Gentzsch | 6-4,6-7,0-0 |
| UTR Pro Tennis Series Mulheim | 2021/10/15 10:00 | Sidane Pontjodikromo v Benjamin Hassan | 6-3,6-3 |
| UTR Pro Tennis Series Mulheim | 2021/10/14 10:00 | Jose Antonio Rodriguez Rodriguez v Benjamin Hassan | 4-6,1-6 |
| UTR Pro Tennis Series Mulheim | 2021/10/12 10:00 | Melchior Delloye v Benjamin Hassan | 1-6,2-5 |
| Challenger Barcelona | 2021/10/03 11:45 | Bekkhan Atlangeriev v Benjamin Hassan | 6-2,3-6,6-1 |
| Challenger Lisbon | 2021/09/30 09:30 | Dmitry Popko v Benjamin Hassan | 6-2,6-4 |
| ITF M25 Columbus | 2021/11/19 14:50 | Alafia Ayeni v Taha Baadi | 5-7,1-6 |
| ITF M25 Columbus | 2021/11/18 18:25 | Alafia Ayeni v Kweisi Kenyatte | 6-3,6-3 |
| ITF M25 Columbus | 2021/11/17 17:10 | Leandro Riedi v Alafia Ayeni | 1-6,6-2,5-7 |
| ITF M15 Ithaca | 2021/10/08 13:55 | Charles Broom v Alafia Ayeni | 3-6,6-3,6-2 |
| ITF M15 Ithaca | 2021/10/05 19:30 | Lorenzo Claverie v Alafia Ayeni | 3-6,4-6 |
| ATP San Diego | 2021/09/26 00:25 | Alafia Ayeni v Alex Bolt | 4-6,6-7 |
| ITF M25 Johannesburg | 2021/09/17 08:00 | Alastair Gray v Alafia Ayeni | 6-2,6-4 |
| ITF M25 Johannesburg | 2021/09/16 08:00 | Francesco Vilardo v Alafia Ayeni | 3-6,6-1,2-6 |