Stadium: Court 3 Round: 44 Ground: Clay
| ITF M15 Heraklion | 2021/11/29 09:00 | Roi Ginat v Dennis Dragomirov | 6-1,6-2 |
| ITF M15 Heraklion | 2021/11/28 11:00 | Artem Dacenko v Dennis Dragomirov | 1-6,3-6 |
| ITF M15 Heraklion | 2021/11/22 08:00 | Alec Deckers v Dennis Dragomirov | 6-2,6-2 |
| ITF M15 Heraklion | 2021/11/21 11:00 | Dennis Dragomirov v Charles Tzicas | 7-6,4-6,10-5 |
| ITF M15 Sharm El Sheikh | 2021/10/26 07:30 | Simonas Zukauskas v Dennis Dragomirov | 7-5,6-3 |
| ITF M15 Sharm El Sheikh | 2021/10/25 08:00 | Dennis Dragomirov v Henrique S Gomes | 6-3,6-4 |
| ITF M15 Sharm El Sheikh | 2021/10/24 09:30 | Bogdan Seleznev v Dennis Dragomirov | 3-6,6-3,8-10 |
| ITF M15 Sharm El Sheikh | 2021/10/18 07:00 | Dennis Dragomirov v Pijus Vaitiekunas | 4-6,4-6 |
| ITF M15 Antalya | 2021/11/15 07:55 | Toby Martin v Petar Jovanovic | 6-4,7-5 |
| ITF M15 Antalya | 2021/11/14 06:30 | Petar Jovanovic v Omar Fields | 6-0,7-5 |
| ITF M15 Antalya | 2021/11/07 06:30 | Toby Martin v Petar Jovanovic | 6-4,3-6,10-7 |
| ITF M15 Antalya | 2021/10/31 07:00 | Pavel Verbin v Petar Jovanovic | 4-6,6-3,10-7 |
| ITF M15 Ulcinj | 2021/09/22 07:55 | Petar Jovanovic v Timo Legout | 0-6,6-2,2-6 |
| ITF M15 Ulcinj | 2021/09/20 11:30 | Alessandro Pecci v Petar Jovanovic | 2-6,0-6 |
| ITF M15 Ulcinj | 2021/09/20 08:00 | Petar Jovanovic v William Ma | 6-0,6-2 |
| ITF M15 Ulcinj | 2021/09/19 08:00 | Petar Jovanovic v Niklas Waldner | 6-3,6-4 |