Stadium: Stadium Round: 25 Ground: Hardcourt outdoor
| WTA - Indian Wells | 2019/03/08 02:00 | Flipkens, Kirsten v Eugenie Bouchard | 7-5,3-6,7-5 |
| Houston, USA | 2019/11/11 17:15 | Valentini Grammatikopoulou v Eugenie Bouchard | 6-7,4-6 |
| ITF W60 Templeton | 2019/09/25 19:35 | Talaba, Gabriela v Eugenie Bouchard | 6-4,4-6,6-4 |
| US Open Women | 2019/08/26 15:00 | Eugenie Bouchard v Anastasija Sevastova | 3-6,3-6 |
| New York, USA | 2019/08/16 19:20 | Kaia Kanepi v Eugenie Bouchard | 6-4,3-6,6-3 |
| Vancouver, Simples W-ITF-CAN-02A | 2019/08/13 20:35 | Eugenie Bouchard v Timea Babos | 6-3,3-6,1-6 |
| WTA Toronto | 2019/08/06 23:00 | Eugenie Bouchard v Andreescu, Bianca Vanessa | 6-4,1-6,4-6 |
| WTA Washington | 2019/07/30 00:30 | Eugenie Bouchard v Lauren Davis | 1-6,2-6 |
| WTA Lausanne | 2019/07/15 15:40 | Tamara Korpatsch v Eugenie Bouchard | 2-6,6-4,7-5 |
| Houston, USA | 2019/11/17 17:00 | Vandeweghe, Coco v Flipkens, Kirsten | 6-7,4-6 |
| Houston, USA | 2019/11/16 19:20 | Flipkens, Kirsten v Falconi, Irina | 6-3,7-5 |
| Houston, USA | 2019/11/15 20:00 | Caty McNally v Flipkens, Kirsten | 5-7,6-4,2-6 |
| Houston, USA | 2019/11/15 16:00 | Bellis, Catherine v Flipkens, Kirsten | 4-6,4-6 |
| Houston, USA | 2019/11/12 21:40 | Hailey Baptiste v Flipkens, Kirsten | 6-3,3-6,6-7 |
| ITF W60 Las Vegas | 2019/11/06 18:45 | Flipkens, Kirsten v Alycia Parks | 4-6,6-3,5-7 |
| ITF W60 Toronto | 2019/11/03 17:00 | Flipkens, Kirsten v Di Lorenzo, Francesca | 6-7,4-6 |
| ITF W60 Toronto | 2019/11/02 17:30 | Flipkens, Kirsten v Murray Sharan, S. | 2-6,6-2,6-3 |