[122] Heather Watson 5-7,1-6 Anett Kontaveit [20] 2019-07-03 12:00
Stadium: Court 1 Round: 24 Ground: Grass
Head to Head
| WTA Brisbane | 2018/01/01 07:50 | Heather Watson v Anett Kontaveit | 0-6,3-6 |
| WTA Luxembourg | 2017/10/18 08:00 | Anett Kontaveit v Heather Watson | 4-6,4-6 |
| WTA Biel | 2017/04/11 10:30 | Anett Kontaveit v Heather Watson | 7-6,6-2 |
Home History
| Wimbledon Women | 2019/07/01 10:00 | Caty McNally v Heather Watson | 6-7,2-6 |
| WTA Eastbourne | 2019/06/23 12:15 | Alize Cornet v Heather Watson | 7-5,6-2 |
| WTA Birmingham | 2019/06/17 13:00 | Heather Watson v Barbora Strycova | 6-3,3-6,4-6 |
| WTA Nottingham | 2019/06/12 14:30 | Maria Sakkari v Heather Watson | 6-4,6-3 |
| ITF W100 Surbiton | 2019/06/08 09:00 | Magdalena Rybarikova v Heather Watson | 6-4,6-4 |
| ITF W100 Surbiton | 2019/06/07 11:30 | Magdalena Rybarikova v Heather Watson | 6-4,4-3 |
| ITF W100 Surbiton | 2019/06/06 10:00 | Madison Brengle v Heather Watson | 4-6,2-6 |
| ITF W100 Surbiton | 2019/06/05 10:25 | Heather Watson v Evgeniya Rodina | 6-4,6-1 |
Away History
| Wimbledon Women | 2019/07/01 11:20 | Shelby Rogers v Anett Kontaveit | 0-6,6-3,4-6 |
| WTA Eastbourne | 2019/06/25 11:45 | Anett Kontaveit v Anna-Lena Friedsam | 3-6,4-6 |
| WTA Eastbourne | 2019/06/23 10:00 | Anett Kontaveit v Harriet Dart | 3-6,6-4,6-2 |
| WTA Birmingham | 2019/06/17 14:50 | Anett Kontaveit v Johanna Konta | 4-6,2-6 |
| French Open Women | 2019/05/28 10:45 | Karolina Muchova v Anett Kontaveit | 3-6,6-2,6-2 |
| WTA Rome | 2019/05/16 12:55 | Anett Kontaveit v Maria Sakkari | 3-6,2-6 |
| WTA Rome | 2019/05/13 15:15 | Anett Kontaveit v Mona Barthel | 4-6,6-4,6-4 |
| WTA Madrid | 2019/05/04 14:40 | Aliaksandra Sasnovich v Anett Kontaveit | 0-6,6-3,6-2 |