| ITF - W25 Boca Raton | 04/11 14:00 | 54 | Taylor Ng v Ena Shibahara | 7-5,4-6,14-16 | |
| ITF W60 - Arcadia | 03/03 20:30 | 27 | [21] Ena Shibahara v Diane Parry [113] | 7-5,6-7,3-6 | |
| ITF W60 - Arcadia | 03/02 19:00 | 26 | Ena Shibahara v Kimmi Hance | 6-1,3-6,6-2 | |
| ITF W60 - Arcadia | 03/01 20:35 | 25 | [283] Francesca Di Lorenzo v Ena Shibahara [21] | 5-7,3-6 | |
| ITF W25 - Burnie | 02/07 23:00 | 25 | [20] Ena Shibahara v Erika Sema [415] | 7-5,4-6,4-6 | |
| ITF W60 - Burnie | 02/02 23:00 | 26 | [174] Priscilla Hon v Ena Shibahara [20] | 6-1,7-5 | |
| ITF W60 - Burnie | 01/31 23:00 | 25 | [20] Ena Shibahara v Hiroko Kuwata [454] | 6-2,6-2 | |
| ITF W60 - Tokyo | 11/15 03:55 | 25 | [22] Ena Shibahara v Misaki Doi [181] | 2-6,4-6 | |
| ITF W60 - Toronto | 10/23 17:15 | 54 | Ena Shibahara v Layne Sleeth | Retired | |
| ITF W60 - Saguenay | 10/20 15:00 | 26 | [21] Ena Shibahara v Karman Kaur Thandi [308] | 2-6,4-6 | |
| ITF W60 - Saguenay | 10/18 13:55 | 25 | Weronika Baszak v Ena Shibahara | 4-6,6-4,2-6 | |
| ITF W60 - Saguenay | 10/17 14:15 | 54 | Ena Shibahara v Alica Rusova | 6-0,6-2 | |
| ITF W60 - Saguenay | 10/16 15:50 | 54 | Ena Shibahara v Brittany Collens | 6-1,6-0 | |
| ITF W25 - Fredericton | 10/12 21:35 | 26 | [13] Ena Shibahara v En Shuo Liang [389] | 1-6,2-6 | |
| ITF W25 - Fredericton | 10/11 17:10 | 25 | Anna Ulyashchenko v Ena Shibahara | 3-6,6-4,1-6 | |
| ITF W80 - Rancho Santa Fe | 10/05 22:00 | 25 | [232] Sophie Chang v Ena Shibahara [12] | 6-1,6-4 | |
| ITF W80 - Rancho Santa Fe | 10/04 18:30 | 54 | [381] Victoria Duval v Ena Shibahara [12] | 3-6,5-7 | |
| ITF W80 - Rancho Santa Fe | 10/03 22:20 | 54 | Megan McCray v Ena Shibahara | 3-6,4-6 | |
| WTA - Tokyo | 09/17 06:40 | 14 | [12] Ena Shibahara v Kyoka Okamura [297] | 1-6,5-7 | |
| WTA - Granby | 08/20 15:00 | 14 | [10] Ena Shibahara v Lulu Sun [353] | 6-3,1-6,2-6 | |
| ITF W25 - Dallas | 07/28 15:00 | 26 | [255] Elvina Kalieva v Ena Shibahara [9] | Retired | |
| ITF W25 - Dallas | 07/27 17:00 | 25 | [9] Ena Shibahara v Victoria Duval [327] | Retired | |
| ITF W25 - Dallas | 07/26 14:00 | 54 | [9] Ena Shibahara v Christina Rosca [226] | 6-1,6-1 | |
| ITF W25 - Dallas | 07/25 17:30 | 54 | Ena Shibahara v Liga Dekmeijere | 6-1,6-1 | |
| ITF W25 - Saskatoon | 07/20 16:00 | 26 | Ena Shibahara v Madison Sieg | 3-6,4-6 | |
| ITF W25 - Saskatoon | 07/18 22:10 | 25 | Ena Shibahara v Martyna Ostrzygalo | 7-6,6-3 | |
| WTA - Rabat | 05/14 12:25 | 14 | [7] Ena Shibahara v Anna Danilina [342] | 2-6,3-6 | |
| ITF W100 - Bonita Springs | 05/02 14:30 | 54 | Sabine Lisicki v Ena Shibahara | 6-3,6-4 | |
| ITF W60 - Charlottesville | 04/19 15:30 | 54 | [232] Gabriela Lee v Ena Shibahara [7] | 6-3,6-1 | |
| ITF W60 - Charlottesville | 04/18 18:00 | 54 | Mara Schmidt v Ena Shibahara | 4-6,2-6 |