Stadium: Court 20 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Doha | 2021/10/03 12:00 | Essa Qabazard v George Gregoriou | 6-0,6-1 |
| ITF M25 Pretoria | 2021/09/26 09:55 | George Gregoriou v Guelord Kayombo | 3-6,0-6 |
| ITF M25 Johannesburg Qual | 2021/09/19 08:50 | Shahar Gabay v George Gregoriou | 6-3,6-4 |
| ITF M15 Cairo | 2021/08/04 14:15 | Juan Bautista Torres v George Gregoriou | 6-2,6-0 |
| ITF M15 Cairo | 2021/07/18 09:30 | Federico Luzzo v George Gregoriou | 6-3,6-2 |
| ITF M25 Belgrade | 2021/06/27 12:00 | Martin Zeljenka v George Gregoriou | 6-1,6-1 |
| ITF M15 Parnu | 2021/10/27 11:55 | Iiro Vasa v Timofey Stepanov | 3-6,6-4,6-2 |
| ITF M15 Parnu | 2021/10/25 10:00 | Igor Shrolik v Timofey Stepanov | 3-6,4-6 |
| ITF M15 Parnu | 2021/10/25 07:00 | Roman Ruenger v Timofey Stepanov | 2-6,1-6 |
| ITF M25 Plaisir | 2021/09/12 09:40 | Nicolas Rousset v Timofey Stepanov | 6-1,6-3 |
| ITF M25 Sierre | 2021/09/01 08:00 | Remy Bertola v Timofey Stepanov | 6-1,6-2 |
| ITF M25 Sierre | 2021/08/30 08:00 | Facundo Yunis v Timofey Stepanov | 6-3,6-3 |
| ITF M25 Sierre | 2021/08/29 10:05 | Tanguy Genier v Timofey Stepanov | 6-4,3-6,8-10 |
| ITF M25 Caslano | 2021/08/23 16:35 | Timofey Stepanov v Gabriele Moghini | 5-7,2-6 |