Chestnut Drive Secondary School
Explore the history of Chestnut Drive Secondary School.
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School History
Chestnut Drive Secondary School, Singapore’s 105th government school, was established in 1968 as a Chinese integrated school with 787 students. It was officially opened on 12 June 1969. Located in Upper Bukit Timah, CDSS was built to serve a vast area, including Woodlands, Choa Chu Kang, Jurong and even Yishun.
In the early years, the school conducted classes for both English and Chinese streams. The Chinese stream was gradually phased out and integrated into a single English stream in 1987. In 1988, the school converted from double session to single session.
In 2002, the school moved into its new campus, which was officially opened on 9 July 2005. At the same time, a new uniform was also launched in 2004.
In 2014, the school was recognised as a Microsoft Mentor School for its innovative best practices in the use of technology for teaching and learning. The school was also awarded the Singapore Book of Records three years in a row for the following projects: ‘Hand to Hand’, the most number of gloves on a display board (2011); ‘Project Run’, the most number of well-wishing cards (2010); and ‘Project Orange Nose’, the most number of people wearing orange noses (2009).
In 2014, the school was accorded the Applied Learning Programme on sustainability. It was based on science, technology, engineering and mathematics as well as humanities applications in the real world.
The school celebrated its 45th anniversary in 2011 with an original musical. In 2016, the school merged with Fajar Secondary School and continued operating under the name of Fajar Secondary School. Chestnut Drive Secondary School’s Chinese name, 励进中学, has since been adopted as the Chinese name of Fajar Secondary School.
Principals:
- Mdm Lo Pui Yu (1968–1976)
- Mr Lim Poh Seng (1977–1980)
- Mr Lee Thiam Lock (1981–1988)
- Mrs Molly Tan (1989)
- Mrs Feng Moh Cheng (1990–1993)
- Mrs Ang Ju Lang (1994–1998)
- Ms Chan Mee Leen (1999–2006)
- Mr Toh Teik Hoe (2007–2012)
- Mdm Tan Miao Ling (2013–2015)
Key Milestones
key milestones
1968 | Establishment of Chestnut Drive Secondary School on 4 January. |
1969 | Official opening of Chestnut Drive Secondary School on 12 June. |
1987 | Integration of Chinese and English streams. |
1988 | Conversion from double session to single session. |
1998 | Celebration of 30th anniversary. |
2002 | Symbolic walk from old campus to new campus on 1 August. |
2005 | Official opening of new campus on 9 July. |
2014 | Designated as Microsoft Mentor School. |
2016 | Merger with Fajar Secondary School to become the present Fajar Secondary |
School Motto
Strive for Excellence
School Crest

The colours of the school badge are blue, red and white. Blue represents tranquillity and peace, red represents universal brotherhood and white stands for purity. The lion symbolises Singapore, while the javelin represents sports and games. The flask and hammer signify science and technology, and the sewing machine represents home economics. The pen and scroll signify academic subjects.
School Song
Chestnut Drive is our school
Its name to us is very dear
We will strive for our school
Be rugged and loyal without fear.
We in Chestnut Drive are proud
We excel in all endeavours
However difficult the task
Chestnut Drive will flourish forever.
Onward Chestnut Drive
We will be loyal and true
Onward Chestnut Drive
We will be faithful to you.


