| WTA Nurnberg | 05/23 09:00 | 26 | [199] Nadia Podoroska v Kirsten Flipkens [69] | 6-7,2-6 | |
| WTA Nurnberg | 05/21 14:25 | 25 | [69] Kirsten Flipkens v Alison Van Uytvanck [46] | 7-6,2-6,7-6 | |
| WTA Madrid Qual | 05/05 12:10 | 46 | [89] Sara Errani v Kirsten Flipkens [73] | 5-7,6-1,6-0 | |
| WTA Madrid Qual | 05/04 15:00 | 45 | [90] Christina McHale v Kirsten Flipkens [73] | 6-7,2-6 | |
| WTA Rabat | 05/02 11:50 | 26 | [96] Ajla Tomljanovic v Kirsten Flipkens [73] | 6-3,6-2 | |
| WTA Rabat | 04/30 14:55 | 25 | [73] Kirsten Flipkens v Petra Martic [40] | 3-6,6-2,6-4 | |
| WTA Istanbul | 04/25 09:30 | 25 | [93] Sara Errani v Kirsten Flipkens [70] | 6-3,6-4 | |
| WTA Lugano | 04/14 08:30 | 27 | [74] Kirsten Flipkens v Vera Lapko [130] | 4-6,6-7 | |
| WTA Lugano | 04/13 12:00 | 26 | [49] Aliaksandra Sasnovich v Kirsten Flipkens [74] | 6-4,4-6,2-6 | |
| WTA Lugano | 04/11 11:30 | 25 | [74] Kirsten Flipkens v Carina Witthoeft [57] | 1-6,6-4,6-3 | |
| WTA Miami | 03/23 18:10 | 24 | [71] Kirsten Flipkens v Johanna Konta [14] | 4-6,3-6 | |
| WTA Miami | 03/20 23:50 | 23 | [71] Kirsten Flipkens v Mihaela Buzarnescu [39] | 6-2,6-3 | |
| WTA Indian Wells | 03/08 20:25 | 23 | Ekaterina Makarova v Kirsten Flipkens | 6-2,6-4 | |
| WTA Budapest | 02/22 11:30 | 26 | Dominika Cibulkova v Kirsten Flipkens | 6-4,6-2 | |
| WTA Budapest | 02/21 09:00 | 25 | Monica Niculescu v Kirsten Flipkens | 3-6,5-7 | |
| 2018 Fed Cup | 02/11 13:40 | 27 | Pauline Parmentier v Kirsten Flipkens | Cancelled | |
| 2018 Fed Cup | 02/10 14:30 | 27 | Kristina Mladenovic v Kirsten Flipkens | 6-2,6-4 | |
| WTA St. Petersburg Qual | 01/27 19:15 | 45 | Kirsten Flipkens v Deborah Chiesa | 2-6,0-6 | |
| Australian Open Women | 01/17 01:30 | 24 | Kirsten Flipkens v Magdalena Rybarikova | 4-6,6-0,2-6 | |
| Australian Open Women | 01/15 00:00 | 23 | Kirsten Flipkens v Alison Riske | 2-6,7-6,6-3 | |
| WTA Hobart | 01/10 02:15 | 26 | Kirsten Flipkens v Alison Riske | Walkover | |
| WTA Hobart | 01/08 03:55 | 25 | Kirsten Flipkens v Kristyna Pliskova | 5-7,7-5,6-3 | |
| WTA Hobart Qual | 01/07 00:25 | 46 | Kirsten Flipkens v Naiktha Bains | 6-4,6-2 | |
| WTA Hobart Qual | 01/06 03:25 | 45 | Kirsten Flipkens v Masa Jovanovic | 6-7,6-1,6-0 | |
| WTA Auckland | 01/03 03:30 | 26 | Kirsten Flipkens v Polona Hercog | 4-6,2-6 | |
| WTA Auckland | 01/01 03:10 | 25 | Donna Vekic v Kirsten Flipkens | 6-7,6-3,4-6 | |
| WTA Luxembourg | 10/16 16:00 | 25 | [58] Beatriz Haddad Maia v Kirsten Flipkens [75] | 6-3,6-4 | |
| WTA Linz | 10/09 16:30 | 25 | [228] Belinda Bencic v Kirsten Flipkens [74] | 4-6,6-2,7-6 | |
| US Open Women | 08/31 23:15 | 24 | [18] Elena Vesnina v Kirsten Flipkens [73] | 6-4,6-4 | |
| US Open Women | 08/30 21:05 | 23 | [81] Madison Brengle v Kirsten Flipkens [73] | 2-6,3-6 |