Stadium: Court 3 Round: 44 Ground: Clay
| ITF M15 Novomoskovsk | 2021/05/23 08:00 | Ivanov, Simon Anthony v Leyton Rivera | 6-4,6-2 |
| ITF M15 Cairo | 2021/05/08 11:05 | Ivanov, Simon Anthony v Oliver Crawford | 7-5,6-4 |
| ITF M15 Cairo | 2021/05/07 08:00 | Carr, Simon v Ivanov, Simon Anthony | 3-6,6-1,1-6 |
| ITF M15 Cairo | 2021/05/06 09:40 | Ivanov, Simon Anthony v Aidan Mchugh | 6-2,6-2 |
| ITF M15 Cairo | 2021/05/05 15:40 | Lorenzo Bocchi v Ivanov, Simon Anthony | 6-4,4-6,2-6 |
| ITF M15 Cairo | 2021/05/04 08:00 | Ivanov, Simon Anthony v Eduardo Ribeiro | 4-6,6-3,10-7 |
| ITF M15 Cairo | 2021/05/03 09:00 | Ivanov, Simon Anthony v Niccolo Catini | 6-2,6-1 |
| ITF M15 Cairo | 2021/05/02 09:00 | Ivanov, Simon Anthony v Guelfo Baldovinetti | 6-3,6-4 |
| ITF M15 Novomoskovsk | 2021/05/23 08:00 | Denis Constantin Spiridon v Illya Maksymchuk | 7-6,3-6,10-8 |
| ITF M15 Cancun | 2020/02/17 14:00 | Spec, Matic v Denis Constantin Spiridon | 6-4,6-1 |