Suécia: Stockholm - Individual - Principal |
| Quartos final | Tipsarevic J. | Sugita Y. | 1:2 (2:6, 6:4, 64:7) | detalhes | 18.10.2019 |
| Oitavos final | Fognini F. | Tipsarevic J. | 0:2 (1:6, 1:6) | detalhes | 17.10.2019 |
| 16avos final | Tipsarevic J. | Moutet C. | 2:0 (6:2, 6:4) | detalhes | 14.10.2019 |
Rússia: St. Petersburg - Individual - Principal |
| 16avos final | Tipsarevic J. | Dzumhur D. | 1:1 RET. (5:7, 6:3, 1:3) | detalhes | 17.09.2019 |
EUA: US Open - Individual - Principal |
| 64avos final | Kudla D. | Tipsarevic J. | 3:1 (3:6, 6:1, 7:65, 6:1) | detalhes | 26.08.2019 |
México: Los Cabos - Individual - Principal |
| 16avos final | Tipsarevic J. | Albot R. | 1:2 (5:7, 6:2, 0:6) | detalhes | 31.07.2019 |
Reino Unido: Wimbledon - Individual - Principal |
| 32avos final | Anderson K. | Tipsarevic J. | 3:1 (6:4, 65:7, 6:1, 6:4) | detalhes | 03.07.2019 |
| 64avos final | Tipsarevic J. | Nishioka Y. | 3:2 (6:4, 62:7, 6:2, 5:7, 6:2) | detalhes | 01.07.2019 |
Reino Unido: Boodles Challenge - Individual - Principal |
| | Broady L. | Tipsarevic J. | 0:2 (3:6, 2:6) | detalhes | 29.06.2019 |
Turquia: Antalya - Individual - Principal |
| 16avos final | Gunneswaran P. | Tipsarevic J. | 2:0 (6:0, 7:66) | detalhes | 24.06.2019 |
França: Open de França - Individual - Principal |
| 64avos final | Tipsarevic J. | Dimitrov G. | 2:3 (3:6, 0:6, 6:3, 7:64, 4:6) | detalhes | 26.05.2019 |
Suiça: Geneva - Individual - Principal |
| Oitavos final | Tipsarevic J. | Dellien H. | 0:2 (63:7, 3:6) | detalhes | 21.05.2019 |
| 16avos final | Gojowczyk P. | Tipsarevic J. | 0:2 (5:7, 5:7) | detalhes | 20.05.2019 |
México: Leon - Individual - Principal |
| 32avos final | Petrovic D. | Tipsarevic J. | CAN. | detalhes | 24.04.2019 |
México: San Luis Potosi - Individual - Principal |
| 16avos final | Miedler L. | Tipsarevic J. | 2:1 (7:5, 3:6, 6:3) | detalhes | 17.04.2019 |
| 32avos final | Tipsarevic J. | Gomez L. | 2:1 (6:4, 5:7, 6:2) | detalhes | 17.04.2019 |
EUA: Houston - Individual - Principal |
| Quartos final | Querrey S. | Tipsarevic J. | 2:0 (7:66, 7:64) | detalhes | 12.04.2019 |
| Oitavos final | Tipsarevic J. | Norrie C. | 2:0 (6:3, 6:4) | detalhes | 11.04.2019 |
| 16avos final | Tipsarevic J. | Sandgren T. | 2:0 (6:1, 7:64) | detalhes | 10.04.2019 |
México: Monterrey - Individual - Principal |
| 16avos final | Polansky P. | Tipsarevic J. | 2:0 (6:3, 6:2) | detalhes | 03.04.2019 |
| 32avos final | Smith R. | Tipsarevic J. | 0:2 (63:7, 4:6) | detalhes | 02.04.2019 |
EUA: Miami - Individual - Principal |
| 32avos final | Bautista R. | Tipsarevic J. | 2:0 (7:63, 6:4) | detalhes | 22.03.2019 |
| 64avos final | Tipsarevic J. | Klahn B. | 2:0 (6:3, 6:3) | detalhes | 20.03.2019 |
Tailândia: Bangkok 2 - Individual - Principal |
| 32avos final | De Bakker T. | Tipsarevic J. | CAN. | detalhes | 19.02.2019 |
Tailândia: Bangkok - Individual - Principal |
| Oitavos final | Duckworth J. | Tipsarevic J. | 2:1 (4:6, 6:3, 6:2) | detalhes | 14.02.2019 |
| 16avos final | Tipsarevic J. | Polmans M. | 2:1 (6:2, 3:6, 6:3) | detalhes | 13.02.2019 |
| 32avos final | Yang T-H. | Tipsarevic J. | 1:2 (2:6, 6:4, 4:6) | detalhes | 12.02.2019 |
Austrália: Australia Open - Individual - Principal |
| 64avos final | Dimitrov G. | Tipsarevic J. | 3:1 (4:6, 6:3, 6:1, 6:4) | detalhes | 14.01.2019 |
Austrália: Kooyong - Individual - Principal |
| | Kubler J. | Tipsarevic J. | 1:2 (4:6, 6:3, 10:12) | detalhes | 08.01.2019 |
EUA: US Open - Individual - Principal |
| 32avos final | Schwartzman D. | Tipsarevic J. | 3:0 (6:2, 6:4, 7:5) | detalhes | 31.08.2017 |
| 64avos final | Kokkinakis T. | Tipsarevic J. | 2:3 (7:65, 6:3, 1:6, 62:7, 3:6) | detalhes | 28.08.2017 |
EUA: Winston-Salem - Individual - Principal |
| 32avos final | Tipsarevic J. | Seppi A. | 0:2 (2:6, 2:6) | detalhes | 21.08.2017 |
EUA: Cincinnati - Individual - Principal |
| 16avos final | Ferrer D. | Tipsarevic J. | 2:1 (6:4, 65:7, 6:1) | detalhes | 16.08.2017 |
EUA: Cincinnati - Individual - Qualificação |
| Final | Tipsarevic J. | Eubanks C. | 0:2 (3:6, 4:6) | detalhes | 13.08.2017 |
| Meias finais | Tipsarevic J. | McNally J. | 2:1 (5:7, 6:1, 7:65) | detalhes | 12.08.2017 |
Reino Unido: Wimbledon - Individual - Principal |
| 64avos final | Tipsarevic J. | Donaldson J. | 0:0 RET. (0:5) | detalhes | 04.07.2017 |