Stadium: Court 5 Round: 25 Ground: Clay
| ITF M15 Antalya | 2021/10/20 07:00 | Santiago De La Fuente v Vladimir Cherkovets | 6-1,6-1 |
| ITF M15 Antalya | 2021/10/12 10:50 | Baran Cengiz v Vladimir Cherkovets | 6-1,6-0 |
| ITF M15 Antalya | 2021/06/20 07:00 | Daniil Savelev v Vladimir Cherkovets | 6-0,6-3 |
| ITF M15 Antalya | 2021/06/13 07:30 | Vladimir Cherkovets v Kaya Arinc | 0-6,1-6 |
| ITF M15 Monastir | 2021/05/23 10:30 | Vladimir Cherkovets v Lucio Carnevalle | 2-6,1-6 |
| ITF M15 Monastir | 2021/04/25 09:00 | Osgar O'Hoisin v Vladimir Cherkovets | 6-2,6-0 |
| ITF M15 Monastir | 2021/04/18 12:00 | Vladimir Cherkovets v Maik Steiner | 1-6,2-6 |
| ITF M15 Monastir | 2021/12/22 09:25 | Nikolay Vylegzhanin v Luca Castagnola | 6-0,6-4 |
| ITF M15 Monastir | 2021/12/20 12:30 | Martyn Pawelski v Luca Castagnola | 4-6,1-6 |
| ITF M15 Monastir | 2021/12/20 08:00 | Thomas George Brun v Luca Castagnola | 1-6,1-6 |
| ITF M15 Monastir | 2021/12/13 13:30 | Ryuki Matsuda v Luca Castagnola | 7-5,6-1 |
| ITF M15 Platja D'Aro | 2021/10/03 09:30 | Max Houkes v Luca Castagnola | 6-4,6-1 |
| ITF M25 Skopje | 2021/09/29 10:30 | Luca Castagnola v Matteo Arnaldi | 2-6,3-6 |
| ITF M25 Skopje | 2021/09/28 09:20 | Luca Castagnola v Sabit Suntic | 6-2,6-3 |
| ITF M25 Skopje | 2021/09/27 12:40 | Tomislav Jotovski v Luca Castagnola | 0-6,4-6 |