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