Stadium: Court 1 Round: 24 Ground: Hardcourt outdoor
| ITF W60 Colina | 2019/11/07 18:15 | Elisabetta Cocciaretto v Valentini Grammatikopoulou | 7-5,6-3 |
| ITF W60 Colina | 2019/11/06 18:00 | Andrea Gamiz v Valentini Grammatikopoulou | 5-7,6-2,5-7 |
| ITF W60 Asuncion | 2019/10/30 19:00 | Valentini Grammatikopoulou v Teliana Pereira | 3-6,2-6 |
| ITF W80 Macon | 2019/10/23 18:30 | Irina Falconi v Valentini Grammatikopoulou | 6-2,6-3 |
| WTA Moscow | 2019/10/13 12:40 | Giulia Gatto Monticone v Valentini Grammatikopoulou | 6-3,5-7,7-6 |
| WTA Moscow | 2019/10/12 16:05 | Elitsa Kostova v Valentini Grammatikopoulou | 3-6,4-6 |
| ITF W60 Caldas da Rainha | 2019/09/25 19:20 | Kaia Kanepi v Valentini Grammatikopoulou | 7-5,6-1 |
| ITF W25 Podgorica | 2019/09/20 09:00 | Amina Anshba v Valentini Grammatikopoulou | 7-5,7-6 |
| ITF W60 Templeton | 2019/09/25 19:35 | Gabriela Talaba 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 |
| WTA New York | 2019/08/16 19:20 | Kaia Kanepi v Eugenie Bouchard | 6-4,3-6,6-3 |
| ITF W100 Vancouver | 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 Bianca Andreescu | 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 |
| Wimbledon Women | 2019/07/02 12:35 | Tamara Zidansek v Eugenie Bouchard | 6-3,5-7,8-6 |