Round: 26 Ground: Hardcourt outdoor
| Challenger Recanati | 2016/07/18 15:30 | Zhyrmont, Dzmitry v Andrea Vavassori | 6-7,6-3,7-6 |
| Challenger Recanati Qual | 2016/07/17 12:30 | Zhyrmont, Dzmitry v Veger, Filip | 5-7,7-5,1-6 |
| ITF Netherlands F4 | 2016/07/06 11:10 | Zhyrmont, Dzmitry v Gijs Brouwer | 5-7,2-6 |
| ITF Netherlands F4 | 2016/07/05 10:00 | Zhyrmont, Dzmitry v Gerritsen, Stephan | 6-4,6-0 |
| Challenger Vicenza Qual | 2016/05/21 14:45 | Lopez Perez v Zhyrmont, Dzmitry | 6-3,6-3 |
| Challenger Ostrava Qual | 2016/04/24 11:00 | Stefano Napolitano v Zhyrmont, Dzmitry | 7-6,4-6,6-3 |
| Challenger St Brieuc Qual | 2016/03/27 09:30 | Zhyrmont, Dzmitry v Rochette, Laurent | 2-6,6-0,5-7 |
| Challenger Wroclaw Qual | 2016/02/13 13:40 | Matteo Berrettini v Zhyrmont, Dzmitry | 7-6,4-6,6-7 |
| Challenger Recanati | 2016/07/19 09:00 | Przysiezny, Michal v Vanni, Luca | 7-6,3-6,5-7 |
| Challenger San Benedetto | 2016/07/12 19:35 | Krawietz, Kevin v Vanni, Luca | 6-4,7-6 |
| Challenger Todi | 2016/07/08 18:15 | Marco Trungelliti v Vanni, Luca | 6-3,7-6 |
| Challenger Todi | 2016/07/07 19:55 | Donati, Matteo v Vanni, Luca | 6-0,5-7,4-6 |
| Challenger Todi | 2016/07/06 19:35 | Arnaboldi, Andrea v Vanni, Luca | 4-6,4-6 |
| Wimbledon Qual | 2016/06/21 14:20 | Zemlja, Grega v Vanni, Luca | 6-3,6-7,6-3 |
| Challenger - Perugia | 2016/06/15 09:00 | Vanni, Luca v Arevalo-Gonzalez, Marcelo | 5-7,6-4,2-6 |
| Challenger - Vicence | 2016/05/25 09:30 | Vanni, Luca v Golubev, Andrey | 5-7,4-6 |