| WTA Houston | 11/15 20:00 | 27 | [117] Catherine McNally v Kirsten Flipkens [94] | 5-7,6-4,2-6 | |
| WTA Houston | 11/15 16:00 | 26 | Catherine Bellis v Kirsten Flipkens | 4-6,4-6 | |
| WTA Houston | 11/12 21:40 | 25 | [279] Hailey Baptiste v Kirsten Flipkens [94] | 6-3,3-6,6-7 | |
| ITF W60 Las Vegas | 11/06 18:45 | 25 | [95] Kirsten Flipkens v Alycia Parks [410] | 4-6,6-3,5-7 | |
| ITF W60 Toronto | 11/03 17:00 | 29 | [99] Kirsten Flipkens v Francesca Di Lorenzo [137] | 6-7,4-6 | |
| ITF W60 Toronto | 11/02 17:30 | 28 | [99] Kirsten Flipkens v Samantha Murray [272] | 2-6,6-2,6-3 | |
| ITF W60 Toronto | 11/01 18:05 | 27 | [99] Kirsten Flipkens v Elitsa Kostova [199] | 6-3,6-2 | |
| ITF W60 Toronto | 10/31 17:15 | 26 | [99] Kirsten Flipkens v Fanni Stollar [321] | 6-2,6-2 | |
| ITF W60 Toronto | 10/30 18:40 | 25 | Kirsten Flipkens v Ariana Arseneault | 6-2,6-1 | |
| WTA Moscow | 10/18 11:25 | 27 | [120] Kirsten Flipkens v Belinda Bencic [10] | 6-7,1-6 | |
| WTA Moscow | 10/16 11:35 | 26 | [28] Dayana Yastremska v Kirsten Flipkens [120] | 3-6,6-3,3-6 | |
| WTA Moscow | 10/15 09:30 | 25 | [120] Kirsten Flipkens v Natalia Vikhlyantseva [93] | 6-3,6-2 | |
| WTA Moscow | 10/14 09:20 | 54 | Kirsten Flipkens v Gabriela Dabrowski | 6-1,6-4 | |
| WTA Moscow | 10/13 09:00 | 46 | Kirsten Flipkens v Liudmila Samsonova | 7-5,6-4 | |
| WTA Moscow | 10/12 08:00 | 45 | [120] Kirsten Flipkens v Anastasia Gasanova [348] | 6-1,6-2 | |
| WTA Linz | 10/06 09:35 | 45 | [101] Kirsten Flipkens v Shelby Rogers [226] | 3-6,2-6 | |
| WTA Tashkent | 09/24 06:30 | 25 | [100] Kirsten Flipkens v Timea Babos [89] | 2-6,5-7 | |
| WTA Seoul | 09/20 08:45 | 27 | [106] Kirsten Flipkens v Magda Linette [48] | 2-6,3-6 | |
| WTA Seoul | 09/18 05:05 | 26 | [56] Margarita Gasparyan v Kirsten Flipkens [106] | 3-6,5-7 | |
| WTA Seoul | 09/17 06:25 | 25 | [255] Denisa Allertova v Kirsten Flipkens [106] | 2-6,5-7 | |
| WTA Hiroshima | 09/12 04:35 | 26 | [63] Alison Van Uytvanck v Kirsten Flipkens [114] | 6-2,3-6,6-3 | |
| WTA Hiroshima | 09/09 06:20 | 25 | [133] Liudmila Samsonova v Kirsten Flipkens [110] | 6-7,4-6 | |
| US Open Women | 08/29 18:35 | 24 | [110] Kirsten Flipkens v Bianca Andreescu [15] | 3-6,5-7 | |
| US Open Women | 08/27 17:20 | 23 | [131] Xiyu Wang v Kirsten Flipkens [110] | 6-3,2-6,2-6 | |
| US Open Women | 08/27 17:00 | 23 | Lesia Tsurenko v Kirsten Flipkens | Cancelled | |
| US Open Women | 08/23 19:05 | 46 | [109] Kirsten Flipkens v Johanna Larsson [172] | 5-7,4-6 | |
| US Open Women | 08/22 15:00 | 45 | [109] Kirsten Flipkens v Jovana Jaksic [244] | 6-2,6-0 | |
| US Open Women | 08/20 21:40 | 44 | [109] Kirsten Flipkens v Irina Bara [192] | 6-3,6-4 | |
| WTA Washington | 07/31 00:50 | 25 | [31] Su-Wei Hsieh v Kirsten Flipkens [106] | 6-4,6-3 | |
| Wimbledon Women | 07/03 10:00 | 24 | [29] Su-Wei Hsieh v Kirsten Flipkens [103] | 7-6,6-3 |