Stadium: Centre Court Round: 29 Ground: Hardcourt indoor
| Challenger Bangkok 4 MD | 2016/01/06 03:00 | Raja/Sharan v Skupski/Skupski | 3-6,6-7 |
| Challenger - Bratislava - HD | 2016/11/11 13:00 | Fyrstenberg/Zimonjic v Skupski/Skupski | 4-6,6-7 |
| Challenger - Ortisei | 2016/11/10 14:35 | Skupski/Skupski v Molchanov/Zelenay | 7-5,6-3 |
| Challenger - Eckental - HD | 2016/11/05 14:30 | Skupski/Skupski v Krawietz/Olivetti | 6-2,3-6,11-13 |
| Challenger - Eckental - HD | 2016/11/03 14:40 | Skugor/Vasilevski v Skupski/Skupski | 2-6,6-4,11-13 |
| ATP - Stockholm - HD | 2016/10/19 11:00 | Pavic/Venus v Skupski/Skupski | 7-6,6-4 |
| Challenger Mons MD | 2016/10/06 12:10 | Knowle/Melzer v Skupski/Skupski | 6-3,4-6,12-10 |
| Challenger Mons MD | 2016/10/04 14:40 | Geens/Reuter v Skupski/Skupski | 0-6,2-6 |
| Challenger - Orleans - HD | 2016/09/26 14:40 | Knowle/Melzer v Skupski/Skupski | 6-4,6-4 |
| Challenger - Ortisei | 2016/11/11 14:35 | Raja/Sharan v Elgin/Istomin | 3-6,7-6,10-3 |
| Challenger - Bratislava - HD | 2016/11/10 13:00 | Knowle/Melzer v Raja/Sharan | 1-6,2-6 |
| Challenger - Bratislava - HD | 2016/11/08 14:15 | Martin/Weissborn v Raja/Sharan | 4-6,0-6 |
| Challenger - Eckental - HD | 2016/11/04 14:20 | Krawietz/Olivetti v Raja/Sharan | 6-4,6-2 |
| Challenger - Eckental - HD | 2016/11/03 13:00 | Marterer/Mies v Raja/Sharan | 6-3,3-6,9-11 |
| Challenger - Pune - HD | 2016/10/29 12:20 | Raja/Sharan v Margaroli/Nys | 3-6,6-3,11-9 |
| Challenger - Pune - HD | 2016/10/28 13:00 | Raja/Sharan v Milojevic/Petrovic | 6-4,6-2 |
| Challenger - Pune - HD | 2016/10/27 11:30 | Raja/Sharan v Deviatiarov/Popko | 7-6,6-4 |