Stadium: Court 4 Round: 27 Ground: Clay
| ITF M15 Cairo | 2021/05/06 08:00 | Simon Carr v Jose Pereira | 2-6,6-4,6-4 |
| ITF M15 Cairo | 2021/05/05 10:00 | Simon Carr v Sherif Makhlouf | 6-4,7-5 |
| ITF M15 New Delhi | 2021/04/03 05:00 | Oliver Crawford v Simon Carr | 6-4,6-3 |
| ITF M15 New Delhi | 2021/04/02 05:30 | Zsombor Velcz v Simon Carr | 3-6,6-2,3-6 |
| ITF M15 New Delhi | 2021/04/01 06:40 | Marco Brugnerotto v Simon Carr | 4-6,3-6 |
| ITF M15 New Delhi | 2021/03/31 05:50 | Aryan Goveas v Simon Carr | 0-6,1-6 |
| ITF M15 Pune | 2021/03/26 04:30 | Jonathan Mridha v Simon Carr | 7-5,2-6,6-1 |
| ITF M15 Pune | 2021/03/25 06:50 | Filip Bergevi v Simon Carr | 2-6,6-7 |
| 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 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/03 11:30 | Martin Dimitrov v Simon A Ivanov | 7-5,2-6,1-5 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/02 08:30 | Dinko Dinev v Simon A Ivanov | 6-2,5-0 |