Chung Cheng High School was first founded by Aw Boon Haw and other philanthropists.

[6] In 1940, the Kuomintang affiliated staff reported the situation to the Chinese government and wished for instructions to close down the school.

To support youths whose education was disrupted by war, the school started accepting students whose ages were older than the average.

[7][8] In 1947, the School Management Board, headed by Lin Shi Wan, acquired a piece of land at Goodman Road for a new premise to cope the increasing student population.

The building incorporated proper educational facilities such as a library, laboratories, and the largest auditorium in Singapore of the time, with a seating capacity of over 2,000.

To complement the 32 classroom block which had been completed in 1995, a 320-seat lecture theatre was added together with other facilities such as computer laboratories, a media resource library, science laboratories, a music room, complete with learning hardware and software, with other special rooms.

[8] In 2001, the school embarked on a project to develop a heritage gallery that would be open to anyone interested in Singapore's history.

In July 2003, the school's heritage gallery was opened by Chan Soo Sen, Minister of State for Education.

In 2003 the school's programmes and processes were acknowledged when it was presented with the Singapore Quality Circle Award for its great contribution to education.

In April 2005, CCHMS was selected to serve as the Centre of Excellence for Chinese in the East Zone (COE), and was awarded the coveted 'School Distinction Award' in recognition of the processes that the school has put in place that lead to sustained achievements in students outcome.

[4] In 2006, the new building for the Centre of Excellence (COE) for Chinese Language and Culture, named the Innosphere, was opened.

At the anniversary gala on 10 July 2014, the Guest of Honour, Prime Minister Lee Hsien Loong, announced that the Administration Building and the Entrance Arch of the school have now been gazetted as a combined national monument.

Prime Minister Lee also opened the Lim Tze Peng art gallery, which is located in the school.

[6] Chung Cheng High (Main)'s uniform consists of a white studded shirt with eight-pleated skirts for female students, shorts for male students in lower secondary levels, or long pants for boys in upper secondary levels.

[4] The Entrance Arch of the school, also a gazetted national monument, features stylised motifs of bats, which represent good fortune and happiness.

Ornamented stone pedestals clad the base of the posts, which are believed to resemble calligraphy brushes.