| Challenger Bangkok 2 | 01/14 05:55 | 29 | Janko Tipsarevic v Zhe Li | 6-2,6-3 | |
| Challenger Bangkok 2 | 01/13 07:15 | 28 | Janko Tipsarevic v Daniel Altmaier | 6-3,6-3 | |
| Challenger Bangkok 2 | 01/12 06:45 | 27 | Janko Tipsarevic v Axel Michon | 6-2,6-2 | |
| Challenger Bangkok 2 | 01/11 04:40 | 26 | Janko Tipsarevic v Sadio Doumbia | 6-3,6-1 | |
| Challenger Bangkok 2 | 01/10 09:00 | 25 | Janko Tipsarevic v Egor Gerasimov | 2-6,6-3,6-3 | |
| Challenger Bangkok | 01/08 04:00 | 29 | Janko Tipsarevic v Blaz Kavcic | 6-3,7-6 | |
| Challenger Bangkok | 01/07 03:00 | 28 | Yuichi Sugita v Janko Tipsarevic | 1-6,6-7 | |
| Challenger Bangkok | 01/06 03:00 | 27 | Yannick Mertens v Janko Tipsarevic | 2-6,4-6 | |
| Challenger Bangkok | 01/04 08:45 | 26 | Cedrik-Marcel Stebe v Janko Tipsarevic | 2-6,3-6 | |
| Challenger Bangkok | 01/03 06:00 | 25 | Jurgen Zopp v Janko Tipsarevic | 4-6,1-6 | |
| Challenger Eckental | 11/02 19:25 | 25 | Janko Tipsarevic v Tobias Kamke | 4-6,3-6 | |
| ATP Moskva | 10/18 11:20 | 25 | Dusan Lajovic v Janko Tipsarevic | 7-6,6-4 | |
| ATP Shanghai | 10/11 10:35 | 25 | Jo-Wilfried Tsonga v Janko Tipsarevic | 6-3,7-6 | |
| ATP Shanghai | 10/09 07:25 | 24 | Janko Tipsarevic v Philipp Kohlschreiber | 6-2,6-4 | |
| ATP Tokyo | 10/06 06:10 | 26 | Ivo Karlovic v Janko Tipsarevic | 7-6,7-6 | |
| ATP Tokyo | 10/04 09:30 | 25 | Janko Tipsarevic v Taro Daniel | 6-2,6-4 | |
| ATP Shenzhen | 10/01 09:00 | 28 | Richard Gasquet v Janko Tipsarevic | Retired | |
| ATP Shenzhen | 09/30 08:25 | 27 | Janko Tipsarevic v Malek Jaziri | 7-6,6-2 | |
| ATP Shenzhen | 09/28 12:00 | 26 | Benoit Paire v Janko Tipsarevic | 0-6,7-6,5-7 | |
| ATP Shenzhen | 09/27 10:00 | 25 | Janko Tipsarevic v Ze Zhang | 7-6,6-4 | |
| ATP St Petersburg | 09/21 10:20 | 25 | Janko Tipsarevic v Mikhail Youzhny | 3-6,5-7 | |
| US Open 2016 | 09/01 16:20 | 24 | Pablo Carreno-Busta v Janko Tipsarevic | 3-6,4-6,6-1,6-4,6-4 | |
| US Open 2016 | 08/30 16:35 | 23 | Janko Tipsarevic v Sam Querrey | 7-6,6-7,6-3,6-3 | |
| Davis Cup | 07/17 16:20 | 1 | Janko Tipsarevic v James Ward | 6-2,3-6,7-5 | |
| Davis Cup | 07/15 14:00 | 1 | Janko Tipsarevic v Kyle Edmund | 3-6,4-6,0-6 | |
| Wimbledon | 06/27 11:55 | 23 | Janko Tipsarevic v Gilles Simon | 6-4,4-6,5-7,3-6 | |
| French Open | 05/23 11:35 | 23 | Milos Raonic v Janko Tipsarevic | 6-3,6-2,7-6 | |
| ATP Genéve | 05/16 13:20 | 25 | Federico Delbonis v Janko Tipsarevic | 6-1,7-6 | |
| Challenger Heilbronn | 05/10 11:55 | 25 | Janko Tipsarevic v Carlos Berlocq | 5-7,3-6 | |
| Challenger Ostrava | 04/26 12:15 | 25 | Janko Tipsarevic v Hans Podlipnik-Castillo | 7-6,3-6,6-4 |