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1. Regional History: 
During the Dutch colonial era, Xiaying District used to be the territory of Madouliao of Madoushe, one of the four major settlements of the Northern Siraya people. During the Jheng Dynasty's rule over Taiwan, the region underwent significant development with the official tuntian system of military encampments at Xiaying Jhuang and Jhongying Jhuang where soldiers worked to clear forests and worked on farmlands. Private clearing also took place at the same time, such as the Han Chinese settlement of Maogangwei that was made possible by settlers who sailed through Cingfongcyue into Wungang to enter Daofong Lagoon.

During the Jheng Dynasty, Taijiang Lagoon was regarded as the center of development. Maogangwei of Xiaying was but an ordinary harbor at Daofong Lagoon. During Qing administration, Taijiang Lagoon began to fill up. The center of development of Han Chinese settlements in southern Taiwan thus began to shift northwards to Daofong Lagoon, allowing Maogangwei to expand and assume the scale of a harbor city that served as a resting point for travelers between Tainan City and Jiayi County. However, Daofong Lagoon itself began to fill up and the port city eventually faded away. Since then, the people of Xiaying has moved inland to clear more farmlands around Daofong Lagoon, creating settlements such as Eliaozai, Dabeiliao, and Datunliao. Settlers also moved westwards to create new districts such as Xiaying, Beimen, Jiangjyun, and Cigu. 


2. Administrative history: 
Under the Jheng Dynasty, administration of Xiaying District was under the jurisdiction of the Maogangwei Bao (an administrative division of 10 families). The Baojhang (head of the Bao) was stationed at Maogangwei Street. Due to poor traffic conditions, the Baojhang requested the County Governor to separate Maogangwei Bao into the two smaller units of East Bao and West Bao, with the West Bao including Xiaying Jhuang, Datunliao, and Dabeiliao regions, while the Baojhang's office was located in Xiaying Jhuang.  
In 1896, the Madou District Office established the Maogangwei Sigang Street District. This district included the Xiaying Jhuang Tongbao, Shihlioujia Jhuang Tongbao, and Datunliao Jhuang. The Jiejhuang District Chief's Office would still be stationed at Xiaying Jhuang. 
In 1908, administrative reforms saw the dissolution of Yanshuei-Cho. This Jiejhuang District thus came under the administration of Tainan-Cho. 
In 1909, Maogangwei Jiejhuang District was renamed the Maogangwei District. 
In 1920, regional system reforms converted this county into Tainan-shu (Tainan Prefecture). Madou branch office was renamed Zengwun County (Soubun Ken). Street reforms were carried out in the same year. Maogangwei District was renamed Xiaying Jhuang, with the central office located at Xiaying. The district would include the five Oaza of Maogangwei, Madouliao, Shihlioujia, Xiaying, and Datunliao. 
When World War II ended in 1945, this township was temporarily renamed Xiaying Jhuang. At that time, there were 3012 households and a total population of 19,324 individuals living in the region. 
In 1946, Taiwansheng Siang Jhen Zujhih Guicheng (Village and Township Organization Procedure of Taiwan Province) named the area as Xiaying Township. No further changes were made to the area of jurisdiction. The Xiaying Oaza (renamed section) included the six villages of Xiaying, Renli, Jhainei, Houjie, Sinsing, and Yingcian (Houjie included part of the Datunliao Oaza, while Sinsing Village included part of the Shihlioujia Oaza). 
Maogangwei Oaza, on the other hand, included the four villages of Maogang, Jhongying, Kaihua, and Silian. Madouliao Oaza included Hejian Village, Shihlioujia Oaza included the two villages of Jiajhong and Hongcuo, while Datunliao Oaza included the two villages of Datun and Dabei. Together, these Oazas accounted for 15 villages that still exist today.