Stadium: Court 3 Round: 25 Ground: Clay
| ITF M15 Sibenik | 2021/04/23 08:00 | Lorenzo Bocchi v David Pichler | 3-6,1-6 |
| ITF M15 Sibenik | 2021/04/22 09:40 | Lilian Marmousez v Lorenzo Bocchi | 6-7,5-7 |
| ITF M15 Sibenik | 2021/04/21 09:20 | Kalin Ivanovski v Lorenzo Bocchi | 7-6,4-6,6-7 |
| ITF M15 New Delhi | 2021/04/02 04:30 | Niki Kaliyanda Poonacha v Lorenzo Bocchi | 6-3,6-7,6-3 |
| ITF M15 New Delhi | 2021/03/30 09:20 | Dhruv Sunish v Lorenzo Bocchi | 6-7,0-6 |
| ITF M15 Pune | 2021/03/24 04:00 | Lorenzo Bocchi v Manish Sureshkumar | 1-6,4-6 |
| ITF M15 Indore | 2021/03/12 04:00 | Eric Vanshelboim v Lorenzo Bocchi | 1-6,7-6,6-1 |
| ITF M15 Indore | 2021/03/11 04:00 | Lorenzo Bocchi v Jonathan Mridha | 7-6,3-6,6-4 |
| 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 |
| UTR Pro Tennis Series Pazardzhik | 2021/03/29 08:00 | Simon A Ivanov v Dragos Dima | 2-6,4-5 |
| ITF M15 Antalya | 2021/02/14 12:00 | Simon A Ivanov v Damien Wenger | 6-2,2-6,6-10 |