| 2013-10-21 | Valencia | Hard | R32 | 35 |  Marcel Granollers | 28 |  Janko Tipsarevic | 1-2 RET | H2H | 3 | 19 | 0 | 0 | 66.7% | 100.0% | 0.0% | 0/0 |
| 2013-10-14 | Moscow | Hard | R16 | 808 |  Karen Khachanov (WC) | 27 | Janko Tipsarevic (3) | 6-4 6-4 | H2H | 3 | 66 | 14 | 4 | 63.5% | 77.5% | 65.2% | 0/0 |
| 2013-10-07 | Shanghai Masters | Hard | R64 | 36 | Marcel Granollers | 24 | Janko Tipsarevic | 6-4 6-4 | H2H | 3 | 85 | 4 | 0 | 65.4% | 85.3% | 66.7% | 1/1 |
| 2013-09-30 | Tokyo | Hard | R16 | 39 |  Alexandr Dolgopolov | 23 | Janko Tipsarevic (8) | 6-3 7-6(2) | H2H | 3 | 75 | 7 | 1 | 57.4% | 80.6% | 73.9% | 1/2 |
| 2013-09-30 | Tokyo | Hard | R32 | 23 | Janko Tipsarevic (8) | 74 |  Victor Hanescu | 6-7(6) 6-1 6-4 | H2H | 3 | 148 | 10 | 3 | 56.3% | 81.0% | 55.6% | 8/8 |
| 2013-09-16 | St. Petersburg | Hard | R32 | 62 | Roberto Bautista Agut | 23 | Janko Tipsarevic (3) | 7-6(4) 6-3 | H2H | 3 | 110 | 6 | 2 | 67.6% | 66.0% | 54.2% | 8/9 |
| 2013-09-13 | Davis Cup WG SF: SRB vs CAN | Clay | RR | 11 |  Milos Raonic | 23 | Janko Tipsarevic | 5-7 6-3 3-6 6-3 10-8 | H2H | 5 | - | - | - | - | - | - | - |
| 2013-09-13 | Davis Cup WG SF: SRB vs CAN | Clay | RR | 23 | Janko Tipsarevic | 41 | Vasek Pospisil | 7-6(3) 6-2 7-6(6) | H2H | 5 | - | - | - | - | - | - | - |
| 2013-08-26 | US Open | Hard | R16 | 4 | David Ferrer (4) | 21 | Janko Tipsarevic (18) | 7-6(2) 3-6 7-5 7-6(3) | H2H | 5 | 237 | 13 | 4 | 65.5% | 73.1% | 46.9% | 9/15 |
| 2013-08-26 | US Open | Hard | R32 | 21 | Janko Tipsarevic (18) | 86 |  Jack Sock | 3-6 7-6(1) 6-1 6-2 | H2H | 5 | 153 | 18 | 2 | 57.0% | 75.4% | 71.7% | 4/5 |
