Stadium: Court 1 Round: 44 Ground: Clay
| ITF M15 Cairo | 2021/05/08 11:05 | Simon A Ivanov v Oliver Crawford | 7-5,6-4 |
| ITF M15 Cairo | 2021/05/07 08:00 | Simon Carr v Simon A Ivanov | 3-6,6-1,1-6 |
| ITF M15 Cairo | 2021/05/06 09:40 | Simon A Ivanov v Aidan Mchugh | 6-2,6-2 |
| ITF M15 Cairo | 2021/05/05 15:40 | Lorenzo Bocchi v Simon A Ivanov | 6-4,4-6,2-6 |
| ITF M15 Cairo | 2021/05/04 08:00 | Simon A Ivanov v Eduardo Ribeiro | 4-6,6-3,10-7 |
| ITF M15 Cairo | 2021/05/03 09:00 | Simon A Ivanov v Niccolo Catini | 6-2,6-1 |
| ITF M15 Cairo | 2021/05/02 09:00 | Simon A Ivanov v Guelfo Baldovinetti | 6-3,6-4 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/04 10:00 | Yurii Dzhavakian v Simon A Ivanov | 6-2,6-4 |
| ITF M15 Monastir | 2021/04/19 12:00 | Leyton Rivera v Fabio Coelho | 4-6,2-6 |
| ITF M15 Monastir | 2021/04/18 10:00 | Leyton Rivera v Jonas Greif | 6-1,6-2 |
| ITF M15 Monastir | 2021/04/12 13:00 | Leyton Rivera v Niklas Schell | 4-6,7-6,8-10 |
| ITF M15 Monastir | 2021/04/12 09:00 | Luca Fantini v Leyton Rivera | 2-6,4-6 |
| ITF M15 Monastir | 2021/04/04 09:00 | Colin Sinclair v Leyton Rivera | 6-2,6-7,10-3 |
| ITF M15 Bratislava | 2021/03/08 09:00 | Neil Oberleitner v Leyton Rivera | 6-4,6-1 |
| ITF M15 Monastir | 2021/03/02 10:35 | Carlos Sanchez Jover v Leyton Rivera | 6-2,6-0 |
| ITF M15 Monastir | 2021/02/21 12:00 | Leyton Rivera v Mirko Martinez | 1-6,2-6 |