Stadium: Court 1 Round: 25 Ground: Hardcourt outdoor
| WTA Toronto | 2019/08/03 18:00 | Nicole Gibbs v Andrea Petkovic | 7-5,4-6,3-6 |
| ITF W60 - Honolulu | 2019/07/14 22:00 | Usue Maitane Arconada v Nicole Gibbs | 6-0,6-2 |
| ITF W60 - Honolulu | 2019/07/13 21:00 | Caroline Dolehide v Nicole Gibbs | 4-6,7-6,4-6 |
| ITF W60 - Honolulu | 2019/07/12 22:00 | Quinn Gleason v Nicole Gibbs | 3-6,1-6 |
| ITF W60 - Honolulu | 2019/07/11 23:20 | Alycia Parks v Nicole Gibbs | 2-6,2-6 |
| ITF W60 - Honolulu | 2019/07/11 00:00 | Sophia Whittle v Nicole Gibbs | 6-7,6-4,3-6 |
| ITF W100 - Bonita Springs | 2019/05/07 23:40 | Robin Anderson v Nicole Gibbs | 2-6,6-4,6-1 |
| ITF W100 - Charleston | 2019/05/03 18:45 | Nicole Gibbs v Kaja Juvan | 1-6,4-6 |
| ITF W100 - Vancouver | 2019/08/12 23:00 | Ena Shibahara v Catherine Harrison | 6-4,6-4 |
| ITF W100 - Vancouver | 2019/08/12 17:00 | Grace Min v Ena Shibahara | 1-6,6-1,10-12 |
| WTA Lausanne | 2019/07/14 10:10 | Allie Kiick v Ena Shibahara | 6-2,6-3 |
| WTA Lausanne | 2019/07/13 14:00 | Renata Voracova v Ena Shibahara | 3-6,3-6 |
| ITF W25 - Karuizawa | 2019/05/22 02:30 | Momoko Kobori v Ena Shibahara | 3-6,7-5,6-3 |
| ITF W25 - Karuizawa | 2019/05/21 04:00 | Ena Shibahara v Asuka Yoshida | 6-1,6-3 |
| ITF W60 - Kurume | 2019/05/17 01:00 | Ena Shibahara v Yuki Naito | 4-6,7-6,2-6 |
| ITF W60 - Kurume | 2019/05/16 01:00 | Ena Shibahara v Alison Bai | 6-3,4-6,6-2 |