| ITF - Nonthaburi W50 | 01/06 03:00 | 28 | [14] Ena Shibahara v Sara Saito [364] | 6-4,1-6,3-6 | |
| ITF - Nonthaburi W50 | 01/05 03:00 | 27 | [14] Ena Shibahara v Catherine Harrison [344] | 6-3,6-3 | |
| ITF - Nonthaburi W50 | 01/04 07:10 | 26 | [14] Ena Shibahara v Thasaporn Naklo [423] | 3-6,7-5,7-5 | |
| ITF - Nonthaburi W50 | 01/03 05:50 | 25 | [266] Mananchaya Sawangkaew v Ena Shibahara [14] | 3-6,6-7 | |
| ITF - Nonthaburi W50 | 01/01 07:00 | 54 | [455] Misaki Matsuda v Ena Shibahara [14] | 2-6,6-4,3-6 | |
| ITF - Nonthaburi W50 | 12/31 09:35 | 54 | [14] Ena Shibahara v Fangzhou Liu [451] | 6-3,6-0 | |
| ITF - Yokohama W40 | 11/29 04:00 | 25 | [14] Ena Shibahara v Sijia Wei [235] | Retired | |
| ITF - Yokohama W40 | 11/28 03:45 | 54 | Ena Shibahara v Hayu Kinoshita | 6-7,6-1,6-4 | |
| ITF - Yokohama W40 | 11/27 06:20 | 54 | Ena Shibahara v Nao Nishino | 6-1,6-3 | |
| ITF - Takasaki W100 | 11/22 01:25 | 25 | Ena Shibahara v Ena Koike | 2-6,0-6 | |
| ITF - Takasaki W100 | 11/21 00:55 | 54 | [269] Eudice Chong v Ena Shibahara [14] | 2-6,4-6 | |
| ITF - Takasaki W100 | 11/20 02:55 | 54 | [14] Ena Shibahara v Ksenia Zaytseva [409] | 6-1,7-6 | |
| ITF - Takasaki W100 | 11/13 02:25 | 54 | [271] Sijia Wei v Ena Shibahara [14] | 6-2,3-6,6-2 | |
| WTA Zhengzhou | 10/07 04:25 | 14 | [103] Tamara Korpatsch v Ena Shibahara [17] | 7-5,6-2 | |
| WTA Tokio | 09/23 06:40 | 14 | [16] Ena Shibahara v Ellen Perez [431] | 6-3,2-6,3-6 | |
| WTA Guadalajara | 09/17 19:05 | 24 | [36] Karolina Pliskova v Ena Shibahara [16] | 7-5,6-2 | |
| WTA Guadalajara | 09/16 19:30 | 19 | [168] Sachia Vickery v Ena Shibahara [16] | 2-6,3-6 | |
| WTA Guadalajara | 09/15 20:25 | 14 | [16] Ena Shibahara v Whitney Osuigwe [363] | 6-1,6-3 | |
| WTA Cleveland | 08/19 16:00 | 14 | [57] Xinyu Wang v Ena Shibahara [15] | 6-2,6-3 | |
| ITF - El Espinar W25 | 07/27 11:30 | 27 | [373] Ekaterina Reyngold v Ena Shibahara [22] | 6-4,7-6 | |
| ITF - El Espinar W25 | 07/26 13:15 | 26 | [22] Ena Shibahara v Anna Brogan [343] | 5-7,6-4,6-1 | |
| ITF - El Espinar W25 | 07/25 11:05 | 25 | [22] Ena Shibahara v Rasheeda McAdoo [264] | 6-3,7-6 | |
| ITF - Porto W40 | 07/19 14:50 | 25 | [22] Ena Shibahara v Lina Glushko [342] | 3-6,4-6 | |
| ITF - Porto W40 | 07/18 14:45 | 24 | Ena Shibahara v Fangran Tian | 6-4,5-7,6-4 | |
| WTA - Strasburg | 05/20 12:55 | 14 | [236] Zhuoxuan Bai v Ena Shibahara [21] | 6-2,6-2 | |
| ITF - Alaminos-Larnaca W25 | 05/04 07:40 | 26 | [203] Raluca Georgiana Serban v Ena Shibahara [21] | 6-2,6-0 | |
| ITF - Alaminos-Larnaca W25 | 05/03 09:20 | 25 | Maria Siopacha v Ena Shibahara | 0-6,7-5,2-6 | |
| ITF - Alaminos-Larnaca W25 | 05/01 09:55 | 15 | Ena Shibahara v Janika Kusy | 6-2,6-3 | |
| ITF - Boca Raton W25 | 04/13 17:05 | 25 | [212] Makenna Jones v Ena Shibahara [21] | Retired | |
| ITF - Boca Raton W25 | 04/11 15:30 | 54 | Ena Shibahara v Hurricane Tyra Black | Retired |