Stadium: CENTER COURT Round: 25 Ground: Hardcourt indoor
| US Open 2016 | 2016/09/01 16:20 | Pablo Carreno Busta v Tipsarevic, Janko | 3-6,4-6,6-1,6-4,6-4 |
| US Open 2016 | 2016/08/30 16:35 | Tipsarevic, Janko v Querrey, Sam | 7-6,6-7,6-3,6-3 |
| Coupe Davis | 2016/07/17 16:20 | Tipsarevic, Janko v Ward, James | 6-2,3-6,7-5 |
| Coupe Davis | 2016/07/15 14:00 | Tipsarevic, Janko v Kyle Edmund | 3-6,4-6,0-6 |
| Wimbledon, London, Great Britain | 2016/06/27 11:55 | Tipsarevic, Janko v Simon, Gilles | 6-4,4-6,5-7,3-6 |
| Open de France | 2016/05/23 11:35 | Milos Raonic v Tipsarevic, Janko | 6-3,6-2,7-6 |
| ATP - Genève | 2016/05/16 13:20 | Delbonis, Federico v Tipsarevic, Janko | 6-1,7-6 |
| Challenger - Heilbronn | 2016/05/10 11:55 | Tipsarevic, Janko v Berlocq, Carlos | 5-7,3-6 |
| US Open 2016 | 2016/08/31 19:10 | Pella, Guido v Youzhny, Mikhail | 2-6,1-6,6-7 |
| US Open, New York, USA | 2016/08/29 15:00 | Youzhny, Mikhail v Martin Klizan | 6-2,6-1,6-1 |
| Cincinnati, USA | 2016/08/17 16:40 | Youzhny, Mikhail v Kei Nishikori | 3-6,2-6 |
| Cincinnati, USA | 2016/08/16 15:00 | Taylor Fritz v Youzhny, Mikhail | 1-6,3-6 |
| ATP Cincinnati Qual | 2016/08/14 22:10 | Youzhny, Mikhail v Baker, Brian | 6-4,6-1 |
| ATP Cincinnati Qual | 2016/08/13 15:20 | Youzhny, Mikhail v Ricardas Berankis | 6-3,6-4 |
| Hamburg, Germany | 2016/07/12 09:00 | Youzhny, Mikhail v Renzo Olivo | 6-7,6-2,1-6 |
| Wimbledon, London, Great Britain | 2016/07/01 14:15 | Alexander Zverev v Youzhny, Mikhail | 6-4,3-6,6-0,4-6,6-2 |