Chung Cheng High School (Chinese: 中正中学) is a Special Assistance Plan (SAP) secondary school in Singapore. It was opened in 1939 at Kim Yam Road by Aw Boon Haw and other businessmen. It started as an all-boys school but became a co-ed school after World War II.
The school is named after Chiang Kai-shek, President of the Republic of China from 1948 to 1975, who is also known as Chiang Chung-cheng.
Chung Cheng High School has a branch school, now known as Chung Cheng High School (Yishun) located at Yishun St. 61. The main school is now located at 40–56 Goodman Road. Both schools are affiliated to Nanyang Junior College. Chung Cheng High School (Main) is renowned for its lake, known as the Zhongzheng Lake (中正湖); its size has been reduced by about two-thirds by several school-expansion programmes since the 1950s. The recent phase of upgrading cost Chung Cheng High School (Main) around $70 million, and saw the renovation of several buildings, such as the Administration Building. The new extension is built on a portion of the lake, with part of the building extending into the lake. The main building has the auditorium which was the largest in the whole Southeast Asia region when it was opened.
Chung Cheng High school (Main) was accorded SAP status in 1979, and achieved autonomous status in 1996 for consistently good O-level results. The school was placed in Band 1 for the recent school ranking exercise 2007. The founding principal, Zhuang Zhulin, was also Principal of Nanyang University. In 2010, the school was awarded with the School Excellence Award, the highest award in the MOE Masterplan of Awards. It serves as a mark of distinction for schools that have achieved excellence in both academic and non-academic outcomes.