Stadium: CENTER Round: 26 Ground: Hardcourt outdoor
| ATP Tokyo | 2016/10/04 05:30 | Karlovic, Ivo v Delbonis, Federico | 7-6,6-7,7-6 |
| US Open 2016 | 2016/09/05 20:05 | Kei Nishikori v Karlovic, Ivo | 6-3,6-4,7-6 |
| US Open 2016 | 2016/09/03 23:45 | Karlovic, Ivo v Donaldson, Jared | 6-4,7-6,6-3 |
| US Open 2016 | 2016/09/02 01:20 | Karlovic, Ivo v Young, Donald | 6-4,7-6,6-4 |
| US Open 2016 | 2016/08/30 19:45 | Karlovic, Ivo v Lu, Yen-Hsun | 4-6,7-6,6-7,7-6,7-5 |
| Cincinnati, USA | 2016/08/16 23:20 | Karlovic, Ivo v MONACO J. | 4-6,4-6 |
| Washington, USA | 2016/07/24 19:00 | Karlovic, Ivo v Gaël Monfils | 7-5,6-7,4-6 |
| Washington, USA | 2016/07/23 18:00 | Steve Johnson v Karlovic, Ivo | 4-6,4-6 |
| ATP Tokyo | 2016/10/04 09:30 | Tipsarevic, Janko v Taro Daniel | 6-2,6-4 |
| ATP Shenzhen | 2016/09/30 08:25 | Tipsarevic, Janko v Jaziri, Malek | 7-6,6-2 |
| ATP Shenzhen | 2016/09/28 12:00 | Benoit Paire v Tipsarevic, Janko | 0-6,7-6,5-7 |
| ATP Shenzhen | 2016/09/27 10:00 | Tipsarevic, Janko v Zhang, Ze | 7-6,6-4 |
| St. Petersburg, Russia | 2016/09/21 10:20 | Tipsarevic, Janko v Youzhny, Mikhail | 3-6,5-7 |
| US Open 2016 | 2016/09/01 16:20 | Carreno-Busta, Pablo 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 |