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