Round: 27 Ground: Hardcourt outdoor
| ITF Belarus F1 | 2016/08/10 07:00 | Dzmitry Zhyrmont v Szymon Walkow | 6-1,6-1 |
| ITF Belarus F1 | 2016/08/08 10:05 | Dzmitry Zhyrmont v Denis Yevseyev | 6-3,2-6,6-4 |
| Challenger Astana 2 | 2016/07/26 08:45 | Blaz Kavcic v Dzmitry Zhyrmont | 6-2,6-2 |
| Challenger Recanati | 2016/07/20 20:00 | Dzmitry Zhyrmont v Luca Vanni | 1-6,7-6,3-6 |
| Challenger Recanati | 2016/07/18 15:30 | Dzmitry Zhyrmont v Andrea Vavassori | 6-7,6-3,7-6 |
| Challenger Recanati Qual | 2016/07/17 12:30 | Dzmitry Zhyrmont v Filip Veger | 5-7,7-5,1-6 |
| ITF Netherlands F4 | 2016/07/06 11:10 | Dzmitry Zhyrmont v Gijs Brouwer | 5-7,2-6 |
| ITF Netherlands F4 | 2016/07/05 10:00 | Dzmitry Zhyrmont v Stephan Gerritsen | 6-4,6-0 |
| ITF Belarus F1 | 2016/08/09 08:15 | Roman Khassanov v Sefa Suluoglu | 6-4,6-2 |
| Challenger Astana 2 | 2016/07/23 09:30 | Vishnu Vardhan v Roman Khassanov | 6-3,6-3 |
| ITF Russia F3 | 2016/07/05 08:45 | Marc Giner v Roman Khassanov | 3-6,6-3,6-1 |
| ITF Russia F3 Qual | 2016/07/04 07:00 | Roman Khassanov v Oleksandr Bielinskyi | 6-3,6-4 |
| ITF Russia F2 Qual | 2016/06/26 09:00 | Roman Khassanov v Mikhail Fufygin | 3-6,4-6 |
| ITF Kazakhstan F4 | 2016/04/27 07:15 | Roman Khassanov v Aleksandre Metreveli | 1-6,3-6 |
| ITF Kazakhstan F4 | 2016/04/26 09:55 | Denis Yevseyev v Roman Khassanov | 7-6,4-6,5-7 |
| ITF Kazakhstan F3 Qual | 2016/04/17 10:15 | Jae-Min Seol v Roman Khassanov | 6-4,3-6,7-6 |