Stadium: Court 2 Round: 28 Ground: Clay
| 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 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/04 10:00 | Dzhavakian, Yurii v Ivanov, Simon Anthony | 6-2,6-4 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/03 11:30 | Dimitrov, Martin v Ivanov, Simon Anthony | 7-5,2-6,1-5 |
| ITF M15 Cairo | 2021/05/07 10:15 | Gabriel Donev v Oliver Crawford | 6-3,2-6,2-6 |
| ITF M15 Cairo | 2021/05/06 09:35 | Thiago Cigarran v Oliver Crawford | 1-6,5-7 |
| ITF M15 Cairo | 2021/05/05 12:45 | Alex Barrena v Oliver Crawford | 0-6,2-6 |
| ITF M15 Cairo | 2021/04/30 09:10 | Oliver Crawford v Malla, Bastian | 1-6,0-6 |
| ITF M15 Cairo | 2021/04/29 08:00 | Oliver Crawford v Galarza, Juan Ignacio | 6-1,6-4 |
| ITF M15 Cairo | 2021/04/28 10:20 | Oliver Crawford v Yanais Laurent | 6-2,6-2 |
| ITF M15 Cairo | 2021/04/25 09:00 | Oliver Crawford v Daniel Michalski | 6-2,5-7,6-3 |
| ITF M15 Cairo | 2021/04/24 09:00 | Benjamin Winter Lopez v Oliver Crawford | 2-6,4-6 |