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