| ITF Women Kashiwa Qual | 04/02 01:00 | 54 | [286] Kai-Chen Chang v Kyoka Okamura [380] | Retired | |
| ITF Women Kashiwa Qual | 04/01 03:30 | 54 | Kai-Chen Chang v Makoto Ninomiya | 6-1,6-7,7-6 | |
| ITF Women Kofu | 03/27 04:20 | 25 | [266] Giulia Gatto Monticone v Kai-Chen Chang [286] | 6-2,6-3 | |
| ITF Women Toyota | 03/14 05:40 | 25 | Kai-Chen Chang v Ayla Aksu | 3-6,2-6 | |
| ITF Women Yokohama | 03/07 05:30 | 25 | Eri Hozumi v Kai-Chen Chang | 7-6,5-7,6-4 | |
| WTA Taipei | 01/31 07:55 | 26 | Yulia Putintseva v Kai-Chen Chang | 6-3,7-6 | |
| WTA Taipei | 01/29 07:30 | 25 | Ya-Hsuan Lee v Kai-Chen Chang | 5-7,2-6 | |
| Australian Open Women WC | 12/01 02:00 | 27 | [119] Misaki Doi v Kai-Chen Chang [223] | 6-3,6-2 | |
| Australian Open Women WC | 11/29 02:00 | 26 | [223] Kai-Chen Chang v Akiko Omae [340] | 6-3,6-3 | |
| WTA Hong Kong | 10/09 11:00 | 25 | [125] Kai-Chen Chang v Qiang Wang [48] | 3-6,0-6 | |
| WTA Beijing Qual | 09/29 06:05 | 45 | [117] Kai-Chen Chang v Magda Linette [83] | 2-6,2-6 | |
| WTA Wuhan Qual | 09/23 08:40 | 46 | [70] Monica Puig v Kai-Chen Chang [120] | 7-6,6-2 | |
| WTA Wuhan Qual | 09/22 07:40 | 45 | [120] Kai-Chen Chang v Madison Brengle [86] | 4-6,6-4,6-2 | |
| WTA Seoul | 09/19 04:55 | 25 | [72] Nao Hibino v Kai-Chen Chang [120] | 6-2,6-4 | |
| WTA Tokyo | 09/11 02:00 | 25 | [41] Kristyna Pliskova v Kai-Chen Chang [113] | 7-5,7-5 | |
| WTA Dalian | 09/05 05:55 | 25 | Vera Zvonareva v Kai-Chen Chang | 6-3,6-7,6-4 | |
| WTA Nanchang | 07/27 09:00 | 26 | [113] Kai-Chen Chang v Yafan Wang [147] | 0-6,2-6 | |
| WTA Nanchang | 07/26 11:05 | 25 | [28] Shuai Zhang v Kai-Chen Chang [113] | 4-6,7-6,4-6 | |
| ITF Women Tianjin | 07/20 02:00 | 26 | [116] Kai-Chen Chang v Jia-Jing Lu [248] | 6-1,5-7,0-6 | |
| ITF Women Tianjin | 07/18 05:40 | 25 | [116] Kai-Chen Chang v Junri Namigata [240] | 6-3,6-3 | |
| Wimbledon Women | 07/03 10:30 | 23 | [111] Kai-Chen Chang v Qiang Wang [55] | 3-6,4-6 | |
| ITF Women Ilkley | 06/22 11:40 | 26 | [98] Maria Sakkari v Kai-Chen Chang [110] | 3-6,6-3,7-6 | |
| ITF Women Ilkley | 06/20 13:20 | 25 | [110] Kai-Chen Chang v Julia Boserup [81] | 4-6,6-0,6-2 | |
| ITF Women Manchester | 06/16 11:25 | 27 | [109] Kai-Chen Chang v Naomi Broady [115] | 3-6,4-6 | |
| ITF Women Manchester | 06/15 10:00 | 26 | [109] Kai-Chen Chang v Katy Dunne [294] | 6-3,4-6,6-1 | |
| ITF Women Manchester | 06/13 12:40 | 25 | [109] Kai-Chen Chang v Danielle Lao [239] | 6-3,6-3 | |
| ITF Women Surbiton | 06/07 16:40 | 25 | [192] Magdalena Rybarikova v Kai-Chen Chang [108] | 6-1,6-3 | |
| French Open Women Qual | 05/25 12:15 | 45 | [108] Kai-Chen Chang v Quirine Lemoine [160] | 2-6,6-2,3-6 | |
| French Open Women Qual | 05/24 09:35 | 44 | [108] Kai-Chen Chang v Tara Moore [145] | 6-2,7-5 | |
| ITF Women Saint Gaudens | 05/16 12:10 | 25 | Kai-Chen Chang v Silvia Soler-Espinosa | 2-6,1-6 |