| WTA Miami | 03/25 17:30 | 24 | [54] Jelena Ostapenko v Kirsten Flipkens [94] | 6-2,5-7,6-3 | |
| WTA Miami | 03/23 14:00 | 19 | [94] Kirsten Flipkens v Aliona Bolsova [109] | 4-6,3-6 | |
| WTA Miami | 03/22 14:00 | 14 | [94] Kirsten Flipkens v Whitney Osuigwe [158] | 4-6,6-3,6-1 | |
| WTA St. Petersburg | 03/16 14:10 | 25 | [69] Katerina Siniakova v Kirsten Flipkens [92] | 6-1,6-2 | |
| Australian Open Women | 02/08 00:00 | 23 | [90] Kirsten Flipkens v Venus Williams [81] | 5-7,2-6 | |
| WTA Yarra Valley Classic | 01/31 03:45 | 24 | Yaroslava Shvedova v Kirsten Flipkens | Cancelled | |
| WTA Abu Dhabi | 01/08 08:10 | 25 | [4] Sofia Kenin v Kirsten Flipkens [86] | Retired | |
| WTA Abu Dhabi | 01/06 10:40 | 24 | [51] Laura Siegemund v Kirsten Flipkens [86] | 7-5,5-7,4-6 | |
| ITF W100 Dubai | 12/09 10:25 | 26 | [59] Heather Watson v Kirsten Flipkens [85] | 6-4,6-2 | |
| ITF W100 Dubai | 12/08 08:15 | 25 | [85] Kirsten Flipkens v Amina Anshba [346] | 6-2,6-2 | |
| ITF W100 Dubai | 12/08 08:00 | 25 | Kirsten Flipkens v Stefanie Voegele | Cancelled | |
| French Open Women | 09/27 16:20 | 23 | [80] Kirsten Flipkens v Yulia Putintseva [27] | 1-6,2-6 | |
| US Open Women | 09/02 17:30 | 24 | [72] Kirsten Flipkens v Jessica Pegula [63] | 6-7,7-6,3-6 | |
| US Open Women | 09/01 00:25 | 23 | [48] Rebecca Peterson v Kirsten Flipkens [72] | 6-7,4-6 | |
| WTA New York | 08/24 15:00 | 25 | [15] Johanna Konta v Kirsten Flipkens [79] | 6-2,6-0 | |
| WTA New York | 08/23 16:45 | 24 | [55] Katerina Siniakova v Kirsten Flipkens [79] | 3-6,3-6 | |
| WTA New York | 08/21 15:00 | 19 | [79] Kirsten Flipkens v Katie Volynets [350] | Retired | |
| WTA New York | 08/20 17:15 | 44 | [79] Kirsten Flipkens v Katarina Zavatska [107] | 5-7,7-5,7-6 | |
| WTA Palermo | 08/04 15:40 | 25 | [77] Kirsten Flipkens v Liudmila Samsonova [117] | 4-6,2-6 | |
| WTA Doha | 02/24 16:05 | 24 | [25] Dayana Yastremska v Kirsten Flipkens [78] | 6-2,6-4 | |
| WTA Doha | 02/22 09:00 | 46 | [83] Kirsten Flipkens v Greet Minnen [106] | 6-1,6-3 | |
| WTA Doha | 02/21 11:00 | 45 | [83] Kirsten Flipkens v Ysaline Bonaventure [117] | 6-3,7-6 | |
| WTA Dubai | 02/16 09:05 | 45 | [81] Kirsten Flipkens v Bethanie Mattek-Sands [385] | 1-6,1-6 | |
| WTA Dubai | 02/15 08:35 | 44 | [81] Kirsten Flipkens v Viktorija Golubic [93] | 6-3,7-5 | |
| 2020 Fed Cup | 02/08 14:30 | - | [81] Kirsten Flipkens v Zarina Diyas [63] | 6-3,6-4 | |
| Australian Open Women | 01/21 06:25 | 23 | [81] Kirsten Flipkens v Karolina Muchova [22] | 3-6,6-2,6-7 | |
| WTA Hobart | 01/14 03:20 | 25 | [79] Kirsten Flipkens v Shuai Zhang [40] | 6-4,3-6,2-6 | |
| WTA Auckland | 01/06 07:40 | 25 | [262] Eugenie Bouchard v Kirsten Flipkens [72] | 7-5,7-5 | |
| WTA Houston | 11/17 17:00 | 29 | [328] Coco Vandeweghe v Kirsten Flipkens [94] | 6-7,4-6 | |
| WTA Houston | 11/16 19:20 | 28 | Kirsten Flipkens v Irina Falconi | 6-3,7-5 |