Round: 25 Ground: Clay
| Challenger Shanghai | 2016/09/06 02:00 | Luca Vanni v Xin Gao | 6-4,3-6,4-6 |
| US Open Qual | 2016/08/23 15:00 | Alejandro Gonzalez v Luca Vanni | 6-4,6-3 |
| Challenger - Segovia | 2016/07/31 11:30 | Luca Vanni v Illya Marchenko | 6-4,3-6,6-3 |
| Challenger - Segovia | 2016/07/30 11:40 | Mirza Basic v Luca Vanni | 4-6,3-6 |
| Challenger - Segovia | 2016/07/29 11:50 | Akira Santillan v Luca Vanni | 6-7,3-6 |
| Challenger - Segovia | 2016/07/27 11:05 | Yannick Mertens v Luca Vanni | 7-6,0-6,3-6 |
| Challenger - Segovia | 2016/07/26 08:30 | Luca Vanni v Jerzy Janowicz | 2-6,7-6,7-5 |
| Challenger Recanati | 2016/07/22 21:30 | Evgeny Donskoy v Luca Vanni | 3-6,6-3,6-0 |
| Challenger Nanchang Qual | 2016/09/11 04:55 | Denys Molchanov v Yusuke Watanuki | 6-3,6-4 |
| Challenger Nanchang Qual | 2016/09/10 09:15 | Denys Molchanov v Ang Ji | 6-1,6-4 |
| Challenger Shanghai | 2016/09/06 02:00 | Denys Molchanov v Jason Jung | 2-6,3-6 |
| Challenger Bangkok 4 | 2016/08/30 07:10 | Denys Molchanov v Amir Weintraub | 5-7,1-6 |
| Challenger Astana 2 | 2016/07/25 06:30 | Denys Molchanov v Edoardo Eremin | 3-6,4-6 |
| Wimbledon Qual | 2016/06/21 13:05 | Nikoloz Basilashvili v Denys Molchanov | 6-2,6-1 |
| Challenger Zhuhai | 2016/03/08 03:05 | Thomas Fabbiano v Denys Molchanov | 6-3,6-7,6-1 |
| Challenger Wroclaw | 2016/02/16 10:00 | Albano Olivetti v Denys Molchanov | 6-2,7-6 |