Stadium: Court 1 Round: 28 Ground: Hardcourt indoor
| ITF W60 Toronto | 2019/11/01 18:05 | Flipkens, Kirsten v Kostova, Elitsa | 6-3,6-2 |
| ITF W60 Toronto | 2019/10/31 17:15 | Flipkens, Kirsten v Fanny Stollar | 6-2,6-2 |
| ITF W60 Toronto | 2019/10/30 18:40 | Flipkens, Kirsten v Arseneault, Ariana | 6-2,6-1 |
| WTA Moscow | 2019/10/18 11:25 | Flipkens, Kirsten v Bencic, Belinda | 6-7,1-6 |
| WTA Moscow | 2019/10/16 11:35 | Dayana Yastremska v Flipkens, Kirsten | 3-6,6-3,3-6 |
| WTA Moscow | 2019/10/15 09:30 | Flipkens, Kirsten v Vikhlyantseva, Natalia | 6-3,6-2 |
| WTA Moscow | 2019/10/14 09:20 | Flipkens, Kirsten v Dabrowski, Gabriela | 6-1,6-4 |
| WTA Moscow | 2019/10/13 09:00 | Flipkens, Kirsten v Samsonova, Liudmila | 7-5,6-4 |
| ITF W60 Toronto | 2019/11/01 15:00 | Indy De Vroome v Murray Sharan, S. | 5-7,6-3,1-6 |
| ITF W60 Toronto | 2019/10/31 15:45 | Murray Sharan, S. v Carter, Hayley | 7-5,7-5 |
| ITF W60 Toronto | 2019/10/30 13:55 | Gleason, Quinn v Murray Sharan, S. | 2-6,4-6 |
| ITF W60 Saguenay | 2019/10/26 16:00 | Robin Anderson v Murray Sharan, S. | 6-1,6-1 |
| ITF W60 Saguenay | 2019/10/25 18:45 | Murray Sharan, S. v Schoofs, Bibiane | 7-6,6-3 |
| ITF W60 Saguenay | 2019/10/24 18:45 | Murray Sharan, S. v Tess Sugnaux | 6-7,7-6,6-4 |
| ITF W60 Saguenay | 2019/10/23 12:45 | Murray Sharan, S. v Viktoria Morvayova | 6-3,1-6,6-3 |
| ITF W25 Cherbourg | 2019/10/11 09:30 | Harmony Tan v Murray Sharan, S. | 6-4,7-5 |