| US Open Women | 08/31 00:20 | 23 | [107] Tsvetana Pironkova v Daria Kasatkina [27] | 2-6,1-6 | |
| Wimbledon Women | 06/30 10:00 | 23 | [103] Tsvetana Pironkova v Yulia Putintseva [43] | 3-6,1-6 | |
| Wimbledon Women | 06/25 10:30 | 19 | [103] Tsvetana Pironkova v Ana Konjuh [129] | 2-6,6-4,2-6 | |
| Wimbledon Women | 06/24 10:00 | 15 | [103] Tsvetana Pironkova v Naiktha Bains [293] | 6-1,6-2 | |
| Wimbledon Women | 06/23 10:00 | 14 | [103] Tsvetana Pironkova v Usue Maitane Arconada [172] | 6-1,6-0 | |
| ITF W100 Nottingham | 06/19 17:10 | 28 | [168] Arina Rodionova v Tsvetana Pironkova [113] | Retired | |
| ITF W100 Nottingham | 06/19 11:35 | 27 | [361] Emma Raducanu v Tsvetana Pironkova [113] | 5-7,6-7 | |
| ITF W100 Nottingham | 06/17 09:55 | 26 | [175] Monica Niculescu v Tsvetana Pironkova [113] | 6-2,3-6,3-6 | |
| ITF W100 Nottingham | 06/15 09:00 | 25 | [113] Tsvetana Pironkova v Nao Hibino [84] | 6-3,6-7,6-3 | |
| French Open Women | 05/26 16:30 | 15 | [116] Tsvetana Pironkova v Susan Bandecchi [219] | 4-6,6-2,3-6 | |
| French Open Women | 05/25 17:05 | 14 | [116] Tsvetana Pironkova v Caroline Dolehide [164] | 6-7,6-2,6-4 | |
| WTA Madrid | 04/27 14:20 | 14 | [54] Anastasija Sevastova v Tsvetana Pironkova [116] | 3-6,6-4,6-3 | |
| WTA Charleston | 04/07 00:50 | 24 | [36] Cori Gauff v Tsvetana Pironkova [113] | 6-3,6-0 | |
| WTA Miami | 03/25 19:05 | 24 | [131] Tsvetana Pironkova v Aryna Sabalenka [8] | 6-0,3-6,6-7 | |
| WTA Miami | 03/24 22:15 | 23 | [131] Tsvetana Pironkova v Marta Kostyuk [85] | 7-6,3-6,6-3 | |
| WTA Miami | 03/23 14:00 | 19 | [143] Olga Govortsova v Tsvetana Pironkova [131] | 0-6,3-6 | |
| WTA Miami | 03/22 15:30 | 14 | [131] Tsvetana Pironkova v Catherine McNally [119] | 7-6,7-6 | |
| Australian Open Women | 02/08 04:05 | 23 | [71] Su-Wei Hsieh v Tsvetana Pironkova [125] | 7-5,6-2 | |
| WTA Yarra Valley Classic | 02/03 07:30 | 26 | [137] Tsvetana Pironkova v Serena Williams [11] | 1-6,4-6 | |
| WTA Yarra Valley Classic | 02/01 03:50 | 25 | [32] Donna Vekic v Tsvetana Pironkova [137] | 6-1,4-6,2-6 | |
| WTA Yarra Valley Classic | 01/31 07:10 | 24 | [136] Tsvetana Pironkova v Liudmila Samsonova [127] | 6-2,6-1 | |
| Australian Open Women | 01/13 06:00 | 19 | [125] Margarita Gasparyan v Tsvetana Pironkova [136] | 3-6,5-7 | |
| Australian Open Women | 01/12 08:00 | 15 | [204] Na-Lae Han v Tsvetana Pironkova [136] | 0-6,6-3,1-6 | |
| Australian Open Women | 01/10 11:40 | 60 | [238] Kyoka Okamura v Tsvetana Pironkova [136] | 0-6,1-6 | |
| French Open Women | 10/02 15:25 | 25 | [114] Barbora Krejcikova v Tsvetana Pironkova [157] | 5-7,6-4,6-3 | |
| French Open Women | 09/30 10:40 | 24 | Tsvetana Pironkova v Serena Williams | Walkover | |
| French Open Women | 09/28 11:05 | 23 | [157] Tsvetana Pironkova v Andrea Petkovic [95] | 6-3,6-3 | |
| US Open Women | 09/09 16:00 | 27 | Tsvetana Pironkova v Serena Williams | 6-4,3-6,2-6 | |
| US Open Women | 09/07 17:35 | 26 | Alize Cornet v Tsvetana Pironkova | 4-6,7-6,3-6 | |
| US Open Women | 09/05 19:55 | 25 | Donna Vekic v Tsvetana Pironkova | 4-6,1-6 |