| WTA New Haven | 08/24 17:00 | 27 | [26] Daria Gavrilova v Kirsten Flipkens [76] | 6-2,6-4 | |
| WTA New Haven | 08/23 16:00 | 26 | [76] Kirsten Flipkens v Ana Bogdan [127] | 6-1,7-6 | |
| WTA New Haven | 08/21 19:05 | 25 | [30] Lesia Tsurenko v Kirsten Flipkens [76] | 2-6,3-6 | |
| WTA New Haven - Qual. | 08/20 15:00 | 46 | [33] Magdalena Rybarikova v Kirsten Flipkens [72] | 3-6,4-6 | |
| WTA New Haven - Qual. | 08/19 17:10 | 45 | [72] Kirsten Flipkens v Tatjana Maria [63] | 6-7,6-3,7-5 | |
| WTA New Haven - Qual. | 08/18 19:00 | 44 | [72] Kirsten Flipkens v Barbora Krejcikova [121] | 6-3,6-1 | |
| WTA Cincinnati Qual | 08/13 15:00 | 45 | [58] Ashleigh Barty v Kirsten Flipkens [82] | 6-1,6-0 | |
| WTA Cincinnati Qual | 08/12 17:20 | 44 | [103] Su-Wei Hsieh v Kirsten Flipkens [82] | 3-6,2-6 | |
| WTA Toronto | 08/09 15:00 | 25 | [82] Kirsten Flipkens v Garbine Muguruza [4] | 5-7,2-6 | |
| WTA Toronto | 08/07 16:30 | 24 | [22] Ana Konjuh v Kirsten Flipkens [82] | Retired | |
| WTA Toronto - Qual. | 08/06 18:05 | 45 | [61] Christina McHale v Kirsten Flipkens [84] | 1-6,7-5,3-6 | |
| WTA Toronto - Qual. | 08/05 22:40 | 44 | Layne Sleeth v Kirsten Flipkens | 2-6,2-6 | |
| Wimbledon Femminile | 07/06 17:10 | 24 | [1] Angelique Kerber v Kirsten Flipkens [88] | 7-5,7-5 | |
| Wimbledon Femminile | 07/04 12:20 | 23 | [88] Kirsten Flipkens v Misaki Doi [57] | 6-4,6-3 | |
| WTA Eastbourne - Qual. | 06/23 16:35 | 45 | [115] Su-Wei Hsieh v Kirsten Flipkens [88] | 5-7,7-6,7-5 | |
| WTA Maiorca | 06/22 13:10 | 26 | [33] Roberta Vinci v Kirsten Flipkens [88] | 6-4,5-7,6-2 | |
| WTA Maiorca | 06/20 10:15 | 25 | [88] Kirsten Flipkens v Mandy Minella [80] | 3-6,6-3,6-2 | |
| WTA Maiorca - Qual. | 06/19 11:25 | 46 | [88] Kirsten Flipkens v Veronika Kudermetova [194] | 4-6,6-0,6-4 | |
| WTA Maiorca - Qual. | 06/18 14:20 | 45 | Kirsten Flipkens v Polina Monova | 6-0,6-3 | |
| WTA Den Bosch | 06/14 15:20 | 26 | [49] Anett Kontaveit v Kirsten Flipkens [75] | 3-6,6-1,6-2 | |
| WTA Den Bosch | 06/13 11:25 | 25 | [75] Kirsten Flipkens v Madison Brengle [83] | 6-1,6-2 | |
| Open di Francia Femminili | 05/31 09:00 | 24 | [22] Samantha Stosur v Kirsten Flipkens [87] | 6-2,7-6 | |
| Open di Francia Femminili | 05/29 14:55 | 23 | [87] Kirsten Flipkens v Mandy Minella [70] | 6-3,6-3 | |
| WTA Norimberga | 05/23 16:10 | 26 | [89] Kirsten Flipkens v Alison Riske [36] | 2-6,2-6 | |
| WTA Norimberga | 05/21 13:30 | 25 | [89] Kirsten Flipkens v Ajla Tomljanovic [304] | 6-2,4-6,6-3 | |
| WTA Madrid - Qual. | 05/05 09:30 | 45 | [92] Kirsten Flipkens v Evgeniya Rodina [78] | 5-7,5-7 | |
| WTA Rabat | 05/01 12:30 | 25 | [71] Varvara Lepchenko v Kirsten Flipkens [93] | 6-3,1-6,6-3 | |
| WTA Istanbul | 04/26 12:50 | 26 | [93] Kirsten Flipkens v Irina-Camelia Begu [33] | 1-6,6-1,3-6 | |
| WTA Istanbul | 04/25 11:55 | 25 | [94] Kristina Kucova v Kirsten Flipkens [93] | Retired | |
| WTA Miami | 03/25 21:10 | 25 | [85] Kirsten Flipkens v Dominika Cibulkova [4] | 2-6,3-6 |