| ATP Stoccolma | 10/18 17:40 | 27 | [251] Janko Tipsarevic v Yuichi Sugita [129] | 2-6,6-4,6-7 | |
| ATP Stoccolma | 10/17 13:50 | 26 | [12] Fabio Fognini v Janko Tipsarevic [251] | 1-6,1-6 | |
| ATP Stoccolma | 10/14 18:40 | 25 | [253] Janko Tipsarevic v Corentin Moutet [97] | 6-2,6-4 | |
| ATP San Pietroburgo | 09/17 10:00 | 25 | [250] Janko Tipsarevic v Damir Dzumhur [86] | Retired | |
| US Open | 08/26 15:00 | 23 | [111] Denis Kudla v Janko Tipsarevic [260] | 3-6,6-1,7-6,6-1 | |
| ATP Los Cabos | 07/31 00:00 | 25 | [256] Janko Tipsarevic v Radu Albot [41] | 5-7,6-2,0-6 | |
| Wimbledon | 07/03 15:45 | 24 | [8] Kevin Anderson v Janko Tipsarevic [288] | 6-4,6-7,6-1,6-4 | |
| Wimbledon | 07/01 10:00 | 23 | [288] Janko Tipsarevic v Yoshihito Nishioka [68] | 6-4,6-7,6-2,5-7,6-2 | |
| Boodles Challenge | 06/29 16:00 | 1 | [287] Liam Broady v Janko Tipsarevic [286] | Cancelled | |
| ATP Antalya | 06/24 10:30 | 25 | [94] Prajnesh Gunneswaran v Janko Tipsarevic [286] | 6-0,7-6 | |
| Open di Francia | 05/26 10:15 | 23 | [317] Janko Tipsarevic v Grigor Dimitrov [47] | 3-6,0-6,6-3,7-6,4-6 | |
| ATP Ginevra | 05/21 18:40 | 26 | [317] Janko Tipsarevic v Hugo Dellien [92] | 6-7,3-6 | |
| ATP Ginevra | 05/20 16:55 | 25 | [96] Peter Gojowczyk v Janko Tipsarevic [317] | 5-7,5-7 | |
| Challenger Leon | 04/23 23:00 | 24 | Danilo Petrovic v Janko Tipsarevic | Cancelled | |
| Challenger San Luis Potosi | 04/17 21:10 | 25 | [257] Lucas Miedler v Janko Tipsarevic [318] | 7-5,3-6,6-3 | |
| Challenger San Luis Potosi | 04/17 00:55 | 24 | Janko Tipsarevic v Lucas Gomez | 6-4,5-7,6-2 | |
| ATP Houston | 04/12 18:30 | 27 | [71] Sam Querrey v Janko Tipsarevic [372] | 7-6,7-6 | |
| ATP Houston | 04/11 17:00 | 26 | [372] Janko Tipsarevic v Cameron Norrie [55] | 6-3,6-4 | |
| ATP Houston | 04/10 00:20 | 25 | [372] Janko Tipsarevic v Tennys Sandgren [81] | 6-1,7-6 | |
| Challenger Monterrey | 04/03 02:10 | 25 | [138] Peter Polansky v Janko Tipsarevic [383] | 6-3,6-2 | |
| Challenger Monterrey | 04/01 22:45 | 24 | [328] Roy Smith v Janko Tipsarevic [383] | 6-7,4-6 | |
| ATP Miami | 03/22 22:45 | 24 | [25] Roberto Bautista-Agut v Janko Tipsarevic [453] | 7-6,6-4 | |
| ATP Miami | 03/20 18:50 | 23 | [453] Janko Tipsarevic v Bradley Klahn [93] | 6-3,6-3 | |
| Challenger Bangkok 1A | 02/19 04:20 | 24 | Thiemo De Bakker v Janko Tipsarevic | Cancelled | |
| Challenger Bangkok | 02/14 06:15 | 26 | James Duckworth v Janko Tipsarevic | 4-6,6-3,6-2 | |
| Challenger Bangkok | 02/13 04:50 | 25 | Janko Tipsarevic v Marc Polmans | 6-2,3-6,6-3 | |
| Challenger Bangkok | 02/12 04:10 | 24 | Tsung-Hua Yang v Janko Tipsarevic | 2-6,6-4,4-6 | |
| Australian Open | 01/14 01:35 | 23 | Grigor Dimitrov v Janko Tipsarevic | 4-6,6-3,6-1,6-4 | |
| Kooyong Classic | 01/08 02:35 | 1 | Jason Kubler v Janko Tipsarevic | 4-6,6-3,10-12 | |
| US Open | 08/30 23:05 | 24 | [33] Diego Schwartzman v Janko Tipsarevic [67] | 6-2,6-4,7-5 |