| ITF M15 Tsaghkadzor Qual | 10/20 13:05 | 44 | Dinko Dinev v Dennis Dragomirov | 6-3,6-3 | |
| ITF M15 Tsaghkadzor Qual | 10/20 06:00 | 44 | Dennis Dragomirov v Samvel Aghayan | 6-3,6-1 | |
| ITF M15 Tsaghkadzor | 10/13 10:40 | 54 | Yvo Panak v Dennis Dragomirov | 7-6,3-6,10-8 | |
| UTR Pro Rome | 09/07 12:09 | - | Dennis Dragomirov v Niccolo Catini | 5-7,4-6 | |
| UTR Pro Rome | 09/06 07:00 | - | Dennis Dragomirov v Eskander Guryev | 6-2,6-1 | |
| UTR Pro Rome | 09/04 15:29 | - | Dennis Dragomirov v Giammarco Gandolfi | 6-2,6-3 | |
| UTR Pro Rome | 09/03 06:00 | - | Dennis Dragomirov v Dzhanashia/Gomez | 0-6,2-6 | |
| UTR Pro Rome | 09/02 11:30 | - | Jean-Christian Morandais v Dennis Dragomirov | 5-7,2-6 | |
| ITF M15 Vienna | 08/25 08:00 | 62 | Paul Roeder v Dennis Dragomirov | Walkover | |
| ITF M15 Kottingbrunn | 08/18 10:30 | 62 | Dennis Dragomirov v Niklas Waldner | 5-7,2-6 | |
| ITF M15 Ollersbach | 08/12 12:00 | 54 | Dennis Dragomirov v Lenny Petit | 6-7,3-6 | |
| ITF M25 Kramsach | 07/21 09:00 | 62 | Maximilian Figl v Dennis Dragomirov | 6-4,6-4 | |
| ITF M15 Hrastnik | 06/03 12:00 | 54 | Jan Kupcic v Dennis Dragomirov | 6-1,6-3 | |
| ITF M15 Osijek | 04/28 07:00 | 62 | Matias Riva v Dennis Dragomirov | 7-6,6-4 | |
| ITF M15 Split | 04/22 08:00 | 62 | Dennis Dragomirov v Karol Filar | 3-6,4-6 | |
| ITF M15 Dubrovnik | 04/14 10:15 | 44 | Dennis Dragomirov v Maks Meh | 6-7,1-6 | |
| ITF M25 Trimbach | 03/11 12:15 | 54 | Tanguy Genier v Dennis Dragomirov | 6-3,6-2 | |
| ITF M15 Oberhaching | 02/11 11:25 | 44 | Jannik Opitz v Dennis Dragomirov | 6-4,6-4 | |
| ITF M25 Heraklion | 11/28 09:30 | 62 | Evgenios Vasilakis v Dennis Dragomirov | 6-2,3-6,14-12 | |
| ITF M25 Heraklion | 11/27 08:00 | 62 | Brett Winters v Dennis Dragomirov | 5-7,1-6 | |
| ITF M15 Heraklion | 11/20 10:00 | 62 | Dennis Dragomirov v Vasil Yehorov | 6-3,3-6,9-11 | |
| ITF M15 Heraklion | 11/19 07:00 | 62 |
SLC Banska Bystrica Women
v
Dennis Dragomirov |
2-6,0-6 | |
| UTR Pro Olomouc | 11/12 07:00 | - | Dennis Dragomirov v Jiri Cizek | 6-3,6-4 | |
| UTR Pro Olomouc | 11/11 07:00 | - | Domagoj Biljesko v Dennis Dragomirov | 3-6,6-7 | |
| UTR Pro Olomouc | 11/10 09:48 | - | Dennis Dragomirov v Oleg Prihodko | 2-6,3-6 | |
| UTR Pro Olomouc | 11/09 10:00 | - | Dennis Dragomirov v Jakub Vrba | 6-3,7-5 | |
| UTR Pro Olomouc | 11/08 07:00 | - | Christos Keisidis v Dennis Dragomirov | 5-7,3-6 | |
| UTR Pro Olomouc | 11/07 11:52 | - | Gabor Mathe v Dennis Dragomirov | 7-6,2-6,4-6 | |
| UTR Pro Nimes | 10/26 11:26 | - | Dennis Dragomirov v Jules Auffray | 6-3,6-7,6-7 | |
| UTR Pro Nimes | 10/25 06:00 | - | Dennis Dragomirov v Nazim Makhlouf | 6-3,6-4 |
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