Sweden: Stockholm - Singles - Main |
| Quarter-finals | Tipsarevic J. | Sugita Y. | 1:2 (2:6, 6:4, 64:7) | details | 18.10.2019 |
| 1/8-finals | Fognini F. | Tipsarevic J. | 0:2 (1:6, 1:6) | details | 17.10.2019 |
| 1/16-finals | Tipsarevic J. | Moutet C. | 2:0 (6:2, 6:4) | details | 14.10.2019 |
Russia: St. Petersburg - Singles - Main |
| 1/16-finals | Tipsarevic J. | Dzumhur D. | 1:1 RET. (5:7, 6:3, 1:3) | details | 17.09.2019 |
USA: US Open - Singles - Main |
| 1/64-finals | Kudla D. | Tipsarevic J. | 3:1 (3:6, 6:1, 7:65, 6:1) | details | 26.08.2019 |
Mexico: Los Cabos - Singles - Main |
| 1/16-finals | Tipsarevic J. | Albot R. | 1:2 (5:7, 6:2, 0:6) | details | 31.07.2019 |
United Kingdom: Wimbledon - Singles - Main |
| 1/32-finals | Anderson K. | Tipsarevic J. | 3:1 (6:4, 65:7, 6:1, 6:4) | details | 03.07.2019 |
| 1/64-finals | Tipsarevic J. | Nishioka Y. | 3:2 (6:4, 62:7, 6:2, 5:7, 6:2) | details | 01.07.2019 |
United Kingdom: Boodles Challenge - Singles - Main |
| | Broady L. | Tipsarevic J. | 0:2 (3:6, 2:6) | details | 29.06.2019 |
Turkey: Antalya - Singles - Main |
| 1/16-finals | Gunneswaran P. | Tipsarevic J. | 2:0 (6:0, 7:66) | details | 24.06.2019 |
France: French Open - Singles - Main |
| 1/64-finals | Tipsarevic J. | Dimitrov G. | 2:3 (3:6, 0:6, 6:3, 7:64, 4:6) | details | 26.05.2019 |
Switzerland: Geneva - Singles - Main |
| 1/8-finals | Tipsarevic J. | Dellien H. | 0:2 (63:7, 3:6) | details | 21.05.2019 |
| 1/16-finals | Gojowczyk P. | Tipsarevic J. | 0:2 (5:7, 5:7) | details | 20.05.2019 |
Mexico: Leon - Singles - Main |
| 1/32-finals | Petrovic D. | Tipsarevic J. | CAN. | details | 24.04.2019 |
Mexico: San Luis Potosi - Singles - Main |
| 1/16-finals | Miedler L. | Tipsarevic J. | 2:1 (7:5, 3:6, 6:3) | details | 17.04.2019 |
| 1/32-finals | Tipsarevic J. | Gomez L. | 2:1 (6:4, 5:7, 6:2) | details | 17.04.2019 |
USA: Houston - Singles - Main |
| Quarter-finals | Querrey S. | Tipsarevic J. | 2:0 (7:66, 7:64) | details | 12.04.2019 |
| 1/8-finals | Tipsarevic J. | Norrie C. | 2:0 (6:3, 6:4) | details | 11.04.2019 |
| 1/16-finals | Tipsarevic J. | Sandgren T. | 2:0 (6:1, 7:64) | details | 10.04.2019 |
Mexico: Monterrey - Singles - Main |
| 1/16-finals | Polansky P. | Tipsarevic J. | 2:0 (6:3, 6:2) | details | 03.04.2019 |
| 1/32-finals | Smith R. | Tipsarevic J. | 0:2 (63:7, 4:6) | details | 02.04.2019 |
USA: Miami - Singles - Main |
| 1/32-finals | Bautista-Agut R. | Tipsarevic J. | 2:0 (7:63, 6:4) | details | 22.03.2019 |
| 1/64-finals | Tipsarevic J. | Klahn B. | 2:0 (6:3, 6:3) | details | 20.03.2019 |
Thailand: Bangkok 2 - Singles - Main |
| 1/32-finals | De Bakker T. | Tipsarevic J. | CAN. | details | 19.02.2019 |
Thailand: Bangkok - Singles - Main |
| 1/8-finals | Duckworth J. | Tipsarevic J. | 2:1 (4:6, 6:3, 6:2) | details | 14.02.2019 |
| 1/16-finals | Tipsarevic J. | Polmans M. | 2:1 (6:2, 3:6, 6:3) | details | 13.02.2019 |
| 1/32-finals | Yang T. | Tipsarevic J. | 1:2 (2:6, 6:4, 4:6) | details | 12.02.2019 |
Australia: Australian Open - Singles - Main |
| 1/64-finals | Dimitrov G. | Tipsarevic J. | 3:1 (4:6, 6:3, 6:1, 6:4) | details | 14.01.2019 |
Australia: Kooyong - Singles - Main |
| | Kubler J. | Tipsarevic J. | 1:2 (4:6, 6:3, 10:12) | details | 08.01.2019 |
USA: US Open - Singles - Main |
| 1/32-finals | Schwartzman D. | Tipsarevic J. | 3:0 (6:2, 6:4, 7:5) | details | 31.08.2017 |
| 1/64-finals | Kokkinakis T. | Tipsarevic J. | 2:3 (7:65, 6:3, 1:6, 62:7, 3:6) | details | 28.08.2017 |
USA: Winston-Salem - Singles - Main |
| 1/32-finals | Tipsarevic J. | Seppi A. | 0:2 (2:6, 2:6) | details | 21.08.2017 |
USA: Cincinnati - Singles - Main |
| 1/16-finals | Ferrer D. | Tipsarevic J. | 2:1 (6:4, 65:7, 6:1) | details | 16.08.2017 |
USA: Cincinnati - Singles - Qualification |
| Final | Tipsarevic J. | Eubanks C. | 0:2 (3:6, 4:6) | details | 13.08.2017 |
| Semi-finals | Tipsarevic J. | McNally J. | 2:1 (5:7, 6:1, 7:65) | details | 12.08.2017 |
United Kingdom: Wimbledon - Singles - Main |
| 1/64-finals | Tipsarevic J. | Donaldson J. | 0:0 RET. (0:5) | details | 04.07.2017 |