| ATP Stockholm | 10/18 17:40 | 27 | [251] Tipsarevic, Janko v Sugita, Yuichi [129] | 2-6,6-4,6-7 | |
| ATP Stockholm | 10/17 13:50 | 26 | [12] Fabio Fognini v Tipsarevic, Janko [251] | 1-6,1-6 | |
| ATP Stockholm | 10/14 18:40 | 25 | [253] Tipsarevic, Janko v Corentin Moutet [97] | 6-2,6-4 | |
| St. Petersburg, Russia | 09/17 10:00 | 25 | [250] Tipsarevic, Janko v Damir Dzumhur [86] | Retired | |
| US Open, New York, USA | 08/26 15:00 | 23 | [111] Denis Kudla v Tipsarevic, Janko [260] | 3-6,6-1,7-6,6-1 | |
| ATP - Los Cabos | 07/31 00:00 | 25 | [256] Tipsarevic, Janko v Radu Albot [41] | 5-7,6-2,0-6 | |
| Wimbledon, London, Great Britain | 07/03 15:45 | 24 | [8] Anderson, Kevin v Tipsarevic, Janko [288] | 6-4,6-7,6-1,6-4 | |
| Wimbledon, London, Great Britain | 07/01 10:00 | 23 | [288] Tipsarevic, Janko 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 Tipsarevic, Janko [286] | Cancelled | |
| Antalya, Turquie | 06/24 10:30 | 25 | [94] Gunneswaran, Prajnesh v Tipsarevic, Janko [286] | 6-0,7-6 | |
| French Open, Paris, France | 05/26 10:15 | 23 | [317] Tipsarevic, Janko v Grigor Dimitrov [47] | 3-6,0-6,6-3,7-6,4-6 | |
| Geneva, Switzerland | 05/21 18:40 | 26 | [317] Tipsarevic, Janko v Hugo Dellien [92] | 6-7,3-6 | |
| Geneva, Switzerland | 05/20 16:55 | 25 | [96] Gojowczyk, Peter v Tipsarevic, Janko [317] | 5-7,5-7 | |
| Challenger Leon | 04/23 23:00 | 24 | Petrovic, Danilo v Tipsarevic, Janko | Cancelled | |
| Challenger - San Luis Potosí | 04/17 21:10 | 25 | [257] Lucas Miedler v Tipsarevic, Janko [318] | 7-5,3-6,6-3 | |
| Challenger - San Luis Potosí | 04/17 00:55 | 24 | Tipsarevic, Janko v Gomez, Lucas | 6-4,5-7,6-2 | |
| ATP - Houston | 04/12 18:30 | 27 | [71] Querrey, Sam v Tipsarevic, Janko [372] | 7-6,7-6 | |
| ATP - Houston | 04/11 17:00 | 26 | [372] Tipsarevic, Janko v Cameron Norrie [55] | 6-3,6-4 | |
| ATP - Houston | 04/10 00:20 | 25 | [372] Tipsarevic, Janko v Tennys Sandgren [81] | 6-1,7-6 | |
| Monterrey, Mexico | 04/03 02:10 | 25 | [138] Polansky, Peter v Tipsarevic, Janko [383] | 6-3,6-2 | |
| Monterrey, Mexico | 04/01 22:45 | 24 | [328] Smith, Roy v Tipsarevic, Janko [383] | 6-7,4-6 | |
| ATP - Miami | 03/22 22:45 | 24 | [25] Bautista-Agut, Roberto v Tipsarevic, Janko [453] | 7-6,6-4 | |
| ATP - Miami | 03/20 18:50 | 23 | [453] Tipsarevic, Janko v Klahn, Bradley [93] | 6-3,6-3 | |
| Bangkok II, Thailand | 02/19 04:20 | 24 | de Bakker, Thiemo v Tipsarevic, Janko | Cancelled | |
| Bangkok, Thaïlande | 02/14 06:15 | 26 | James Duckworth v Tipsarevic, Janko | 4-6,6-3,6-2 | |
| Bangkok, Thaïlande | 02/13 04:50 | 25 | Tipsarevic, Janko v Marc Polmans | 6-2,3-6,6-3 | |
| Bangkok, Thaïlande | 02/12 04:10 | 24 | Yang, Tsung-Hua v Tipsarevic, Janko | 2-6,6-4,4-6 | |
| Open d'Australie | 01/14 01:35 | 23 | Grigor Dimitrov v Tipsarevic, Janko | 4-6,6-3,6-1,6-4 | |
| Kooyong Classic | 01/08 02:35 | 1 | Jason Kubler v Tipsarevic, Janko | 4-6,6-3,10-12 | |
| US Open, New York, USA | 08/30 23:05 | 24 | [33] Diego Schwartzman v Tipsarevic, Janko [67] | 6-2,6-4,7-5 |