Stadium: Court 20 Round: 62 Ground: Hardcourt outdoor
| ITF - M15 Héraklion | 2021/11/15 08:00 | Ivanov, Simon Anthony v Brun, Thomas George | 6-2,6-0 |
| ITF - M15 Héraklion | 2021/11/10 08:30 | Ivanov, Simon Anthony v Weindl, Michael | 7-5,1-6,1-6 |
| UTR Pro Tennis Series Brasov | 2021/10/30 09:30 | Antonescu, Vasile v Ivanov, Simon Anthony | 6-0,6-3 |
| UTR Pro Tennis Series Brasov | 2021/10/27 11:30 | Ivanov, Simon Anthony v Borza, Bogdan | 4-6,2-5 |
| UTR Pro Tennis Series Brasov | 2021/10/26 07:00 | Ivanov, Simon Anthony v Ilya Snitari | 5-7,3-6 |
| UTR Pro Tennis Series Brasov | 2021/10/25 08:30 | Ivanov, Simon Anthony v Samuil Konov | 6-4,6-2 |
| ITF M15 Sozopol | 2021/10/13 10:00 | Ivanov, Simon Anthony v Petr Nesterov | 3-6,2-6 |
| ITF M15 Sozopol | 2021/10/07 07:00 | Tim Handel v Ivanov, Simon Anthony | 7-5,6-2 |
| ITF - M15 Héraklion | 2021/11/15 08:00 | Panagoulopoulos, Gosse v Gianluca Coloma-Heck | 2-6,1-6 |
| ITF - M15 Héraklion | 2021/11/14 07:00 | Gianluca Coloma-Heck v Macovei, Radu Florin | 6-2,6-2 |
| ITF - M15 Héraklion | 2021/11/07 11:00 | Gianluca Coloma-Heck v Kim, Dong Ju | 2-6,1-6 |
| ITF M15 Sozopol | 2021/10/10 09:00 | Penev, Ivan v Gianluca Coloma-Heck | 6-1,6-3 |
| ITF M15 Sozopol | 2021/10/03 07:00 | Wojcik, Yann v Gianluca Coloma-Heck | 6-1,7-5 |
| ITF - M15 Monastir | 2021/08/22 10:00 | Mohamed Amin Oueslati v Gianluca Coloma-Heck | 3-6,6-4,10-5 |
| ITF - M15 Monastir | 2021/08/15 07:30 | Gianluca Coloma-Heck v Syed Naguib, Syed Mohd Agil | 4-6,2-6 |
| ITF M25 Jablonec Nad Nisou | 2021/05/18 07:30 | Stanek, Robin v Gianluca Coloma-Heck | 6-1,6-1 |