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At the end of 1938, plans for building the school were revealed.
Construction started at 60 Kim Yam Road in 1939. The school's original name in English was Chiang Kai Sek Secondary School. The founding principal of the school was Dr. Chuang Chu Lin and the first School Supervisor was Mr. Lim Bo Seng, the hero who sacrificed himself to defend Singapore during the period of Japanese Invasion. The school's founding Chairman of the School Management Board was Mr. Aw Boon Haw. In 1940, Mr. Xie Rongxi took over the appointment of Chairman of the School Management Board from Mr. Aw.
Guided by the philosophy of providing education to all without discrimination, the school admitted students from different strata of the society. Students came as far as Thailand and the Philippines. With the invasion by the Japanese in 1942, the school was forced to discontinue.
After the 2nd World War, the school resumed, taking in female students. Mr. Xie Rongxi was re-appointed as Chairman of the Management Committee and Dr. Chuang Chu Lin was re-appointed principal.
In the first national examination after the war, the school achieved top honours among Singapore schools. The student population increased so much that Mr. Lin Shi Wan, Chairman of the Management Board, bought a piece of land at Goodman Road, naming it Chung Cheng High (Main) while calling the one at Kim Yam Road Chung Cheng High (Branch).
In 1953, Mr. Chen Wenque took over as Chairman of the Management Board and improved the school facilities. A few principals, with short stints of office, headed the school in the late 1950s.
1957 Jul - Dec 1: Mr. Shen Weilin (Appointed as Chairman of the School Executive Committee, covering the duties of Dr. Chuang Chu Lin in his absence. )
1958-1959 : Mr. Wang Changji
1960 Jan - Sep : Mr. Lin Yuji
1960 Sep - Dec : Mr. Lin Qiyuan
During this period, three principals served the school for more than 6 years each:
1961 - 1967 : Mr. Huang Faggui
1967 May – Aug : Mr. Yao Fusen (acting principal)
1967 – 1974 : Mr. Qiu Xinmin
1974 – 1981 : Mr. Chia Thiam Soon
In 1965, Mr Goh Tjioe Kok JP BBM was appointed Chairman of the School Management Committee.
After Singapore's independence, bilingualism as well as science and technology were given great impetus. The school upgraded its facilities, building an auditorium in 1968 and a Science and Technology Block in 1975.
1981 -1990
One of the most significant events in the history of the school happened in 1979. The school was given SAP status. Under the SAP scheme, the school offered both English and Chinese as first languages to Special Stream students. In April 1981 Mr. Goh Seow Chew was appointed the Principal of the school, succeeding Mr. Chia Thiam Soon.
1982 saw the first batch of the Special Stream students taking their 'O' Levels. Results were commendable.
Work on the building of the Craft-cum-Technical Complex began in 1990 and was completed by 1992. That same year, Chung Cheng High School (Main) achieved very good results in the GCE 'O' Level Examination and was one of the 'value-added' SAP schools. It continued to achieve outstanding GCE 'O' Level results in 1993 and was ranked among the top 10 'value-added' schools.
 With the demise of Mr. Goh Tjioe Kok in 1994, Mr. Wee Cho Yaw was elected Chairman of the School Management Committee (SMC). Under his leadership, the school embarked on an ambitious upgrading programme.
In 1995, Mr. Yang Che Kay was appointed principal of the school, taking over from Mr. Goh Seow Chow who retired that same year.
Due to its consistently good performance in the GCE 'O' Level Examinations, the school achieved autonomous status in 1996.
The third phase of the school development ended in 1999. To complement the 32 classroom block which had been completed in 1995, a 320-seater lecture theatre was constructed, together with computer laboratories, science laboratories, a Media Resource Library, and a music room, so as to maximize the potential of every pupil. Near the famous Chung Cheng lake, tennis courts and street soccer court were built to add to the vibrancy of the sprawling campus. The Grand Hall was also refurbished with new seats and parquet flooring, increasing its seating capacity to 2000.
At the end of 2000, Mr. Yang Che Kay left to assume the position of Cluster Superintendent of West 5 Cluster. The school's SMC supervisor, Mr. Lee Chin Chuan, having served in the post for more than two decades, also stepped down that year. He was succeeded in June 2000 by Mr. Jimmy Koh, a supportive old boy of the school.
In Dec 2000, Mr. Yue Lip Sin became principal of Chung Cheng High (Main). Together with the staff, he set out his strategic plans to meet the demands of the 21st Century. This was appropriately encapsulated by the acronym "DEBEST", which stood for Developing Character, Energising Curriculum, Building Capacity, Empowering Staff and Strengthening Partnership.
To reflect the glorious past of the school and celebrate the school's involvement in education, the school embarked on an ambitious project to develop a heritage gallery, that would not just be for people associated with Chung Cheng High School but for anyone interested in Singapoer's history. In July 2003, the school's heritage gallery was opened by Mr. Chan Soo Sen, Minister of State of Education. It was the largest of its kind to be developed in a school and boasted a rich array of historical artifacts, photographs and even IT presentations.
2003 marked a new phase in the school's development as the school was also acknowledged for its outstanding programmes and processes as it was presented with the Singapore Quality Circle Award for its great contribution to education. The school also received the MOE Thinking Culture (Best Schools) awards for three consecutive years (2002 – 2004). In May 2004, we were the first school to put up a full performance at the world-class Theatre @ the Esplanade, for it, we received rave reviews from the audience. In Dec 2004, Mr Yue was promoted to spearhead the Committee to Promote Chinese Language Learning (CPCLL) as the Deputy Director for Languages and Literature, Curriculum Planning and Development Division at MOE HQ. After Mr Yue’s embarkment for the new post, Mr Lo Chee Lin was appointed Principal of the school. But he is no stranger to the school as he was the Vice-Principal here from 1995 to 1996.
The school successfully launched its 4-year Chinese Studies Programme (CSP) in January 2005 to provide pupils opportunities to increase their exposure and have a deeper appreciation of the Chinese culture.
In April 2005, Chung Cheng was selected to serve as the Centre of Excellence for Chinese in the East Zone (COE). The renovation of our CCA block began in July to make way for the centre.
2005 also saw Chung Cheng gaining a place in global history by settling a new Guinness World Record for the longest can-chain that was previously set by South Africa’s Aurora School. This project was undertaken in a bid to inculcate environmental awareness and to raise funds for the needy.
The school was awarded the coveted ‘School Distinction Award’ in recognition of the well-defined processes that the school has put in place that lead to sustained achievements in students outcome.
In 2006, Innosphere, the name coined for this new Centre (COE), was opened with its comprehensive facilities such as a library for Chinese language resources, teahouse and a state-of-art auditorium. It serves as a popular venue for seminars, workshops, exhibitions and performances. Besides, the centre houses all the aesthetics CCA under one roof, in conjunction with the plan to develop our niche areas in the aesthetics programmes. With the aim of promoting a deeper understanding of the Chinese culture, our school was also involved in a twinning programme with reputable schools in China.
With every new venture that Chung Cheng staff and students embark on, we look forward to gain, enrich and refine our learning experiences. Through it all, the Chung Cheng Spirit remained indefatigable in seeking to develop our students’ potential and scale new heights in an ever-changing world.
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