[81] Kirsten Flipkens 3-6,4-6 Caroline Wozniacki [14] 2019-06-24 15:55
Stadium: Centre Court Round: 24 Ground: Grass
Home History
| WTA Mallorca | 2019/06/17 14:50 | Sofia Kenin v Kirsten Flipkens | 6-2,6-3 |
| WTA Hertogenbosch | 2019/06/14 16:55 | Kirsten Flipkens v Elena Rybakina | 4-6,4-6 |
| WTA Hertogenbosch | 2019/06/12 14:00 | Lesia Tsurenko v Kirsten Flipkens | 6-7,5-7 |
| WTA Hertogenbosch | 2019/06/11 09:00 | Kirsten Flipkens v Aleksandra Krunic | 6-3,3-6,6-1 |
| French Open Women | 2019/05/28 09:00 | Monica Puig v Kirsten Flipkens | 6-1,7-5 |
| WTA Nurnberg | 2019/05/22 08:30 | Sorana Cirstea v Kirsten Flipkens | 7-6,6-2 |
| WTA Madrid | 2019/05/04 12:35 | Kirsten Flipkens v Anastasija Sevastova | 6-0,3-6,2-6 |
| WTA Rabat | 2019/04/30 16:35 | Elise Mertens v Kirsten Flipkens | 6-3,6-1 |
Away History
| French Open Women | 2019/05/27 09:00 | Caroline Wozniacki v Veronika Kudermetova | 6-0,3-6,3-6 |
| WTA Charleston | 2019/04/07 17:00 | Madison Keys v Caroline Wozniacki | 7-6,6-3 |
| WTA Charleston | 2019/04/06 17:00 | Petra Martic v Caroline Wozniacki | 3-6,4-6 |
| WTA Charleston | 2019/04/05 18:40 | Caroline Wozniacki v Maria Sakkari | 6-2,6-2 |
| WTA Charleston | 2019/04/04 18:55 | Caroline Wozniacki v Mihaela Buzarnescu | 6-4,3-6,6-3 |
| WTA Charleston | 2019/04/03 20:35 | Caroline Wozniacki v Laura Siegemund | 6-2,6-2 |
| WTA Miami | 2019/03/25 19:55 | Su-Wei Hsieh v Caroline Wozniacki | 6-3,6-7,6-2 |
| WTA Miami | 2019/03/23 20:20 | Monica Niculescu v Caroline Wozniacki | 4-6,6-7 |