| US Open, New York, USA | 08/28 19:35 | 23 | [222] Thanasi Kokkinakis v Tipsarevic, Janko [67] | 7-6,6-3,1-6,6-7,3-6 | |
| Winston-Salem, USA | 08/21 19:00 | 24 | [66] Tipsarevic, Janko v Seppi, Andreas [86] | 2-6,2-6 | |
| Cincinnati, USA | 08/16 15:00 | 25 | [31] FERRER D. v Tipsarevic, Janko [69] | 6-4,6-7,6-1 | |
| ATP Cincinnati Qual | 08/13 19:40 | 46 | [58] Tipsarevic, Janko v Christopher Eubanks [374] | 3-6,4-6 | |
| ATP Cincinnati Qual | 08/12 21:25 | 45 | Tipsarevic, Janko v Mcnally, John | 5-7,6-1,7-6 | |
| Wimbledon, London, Great Britain | 07/04 17:45 | 23 | [63] Tipsarevic, Janko v Donaldson, Jared [67] | Retired | |
| Antalya, Turquie | 06/28 11:00 | 26 | [61] Tipsarevic, Janko v Seppi, Andreas [102] | 6-3,4-6,4-6 | |
| Antalya, Turquie | 06/27 11:00 | 25 | [257] Lloyd Harris v Tipsarevic, Janko [61] | 5-7,3-6 | |
| Antalya, Turquie | 06/27 07:00 | - | Karen Khachanov v Tipsarevic, Janko | Cancelled | |
| London, Great Britain | 06/20 13:30 | 25 | [39] Troicki, Viktor v Tipsarevic, Janko [59] | 5-7,7-6,7-6 | |
| ATP Den Bosch | 06/15 10:30 | 26 | [7] Marin Cilic v Tipsarevic, Janko [61] | 6-7,6-2,6-4 | |
| ATP Den Bosch | 06/13 14:40 | 25 | [64] Sugita, Yuichi v Tipsarevic, Janko [61] | 6-7,6-3,0-6 | |
| Open de France | 05/29 10:40 | 23 | [59] Joao Sousa v Tipsarevic, Janko [58] | 4-6,7-6,6-2,6-2 | |
| ATP - Genève | 05/24 14:10 | 26 | [314] Stebe, Cedrik-Marcel v Tipsarevic, Janko [61] | Retired | |
| ATP - Genève | 05/23 12:35 | 25 | [61] Tipsarevic, Janko v Harrison, Ryan [42] | 6-4,7-6 | |
| Anning, China | 04/30 04:45 | 29 | [129] Quentin Halys v Tipsarevic, Janko [71] | 7-6,3-6,4-6 | |
| Anning, China | 04/29 06:40 | 28 | [364] Juan Pablo Paz v Tipsarevic, Janko [71] | 4-6,3-6 | |
| Anning, China | 04/28 04:10 | 27 | Kavcic, Blaz v Tipsarevic, Janko | 1-6,4-6 | |
| Anning, China | 04/28 04:05 | - | [128] Kavcic, Blaz v Tipsarevic, Janko [71] | 1-6,4-6 | |
| Anning, China | 04/26 04:15 | 26 | [166] Jason Jung v Tipsarevic, Janko [71] | 5-7,2-6 | |
| Anning, China | 04/25 07:35 | 25 | [431] Fajing Sun v Tipsarevic, Janko [71] | 0-6,4-6 | |
| Challenger Qingdao | 04/23 03:00 | 29 | [367] Oscar Otte v Tipsarevic, Janko [89] | 3-6,6-7 | |
| Challenger Qingdao | 04/22 04:45 | 28 | [151] Mathias Bourgue v Tipsarevic, Janko [89] | 3-6,4-6 | |
| Challenger Qingdao | 04/21 04:15 | 27 | [123] Andrej Martin v Tipsarevic, Janko [89] | 4-6,1-6 | |
| Challenger Qingdao | 04/20 04:40 | 26 | [179] Ilya Ivashka v Tipsarevic, Janko [89] | 3-6,3-6 | |
| Challenger Qingdao | 04/18 03:55 | 25 | Munoz-De la Nava, Daniel v Tipsarevic, Janko | 3-6,6-7 | |
| ATP - Rio De Janeiro | 02/22 00:05 | 25 | [96] Tipsarevic, Janko v Dominic Thiem [8] | 4-6,5-7 | |
| ATP - Buenos Aires | 02/14 18:30 | 25 | Dolgopolov, Aleksandr v Tipsarevic, Janko | 6-3,6-3 | |
| Quito, Ecuador | 02/08 21:25 | 26 | Bellucci, Thomaz v Tipsarevic, Janko | 7-6,7-6 | |
| Quito, Ecuador | 02/06 21:10 | 25 | Gimeno-Traver, Daniel v Tipsarevic, Janko | Retired |