Chestnut Drive Secondary School (CDSS) received her first cohort of students on 4 January 1968. She started as a Chinese Integrated School with an enrolment figure of 787. The school was officially opened by then Member of Parliament, Mr. P. Selvadurai on 12 June 1969.
The school is situated in a choice private residential district in Upper Bukit Timah. It was built to serve a vast area, with students coming from Woodlands, Jurong, Bukit Batok, Choa Chu Kang and even Yishun.
The school conducted classes for both the English and Chinese streams in her early years until 1988 when the Chinese Stream was phased out due to the implementation of the national curriculum.
The School Advisory Committee and Pupil Welfare Fund were set up in the 1970s during the tenure of the first principal, Mdm. Lo Pui Yu. The school song was composed in 1976 by the third Principal, Mr. Lee Thiam Lock.
Under the stewardship of the seventh Principal, Ms. Chan Mee Leen, the school underwent a phased reconstruction which was completed in 2005. On 9 July 2005, the new campus was declared officially opened by Dr. Teo Ho Pin, Mayor of North-West District and Member of Parliament for Holland-Bukit Panjang GRC. In 2011, the school celebrated its 45th anniversary with an original musical.
On 15 December 2012, Mdm Tan Miao Ling was appointed the ninth Principal of CDSS, taking the mantle from Mr. Teoh Teik Hoe.
In late 2014, the school started her preparations for merger with Fajar Secondary School to become Fajar Secondary School, 励进中学, from 1 January 2016. On 21 November 2015, the school finally closed her doors with a fitting function “Celebrations 2015” where CDSS ex School Leaders, Pioneer Teachers, Senior Educators, ex-staff and ex-students attended. The function was graced by Ms Sim Ann, Senior Minister of State, Ministry of Culture, Community and Youth & Ministry of Finance and MP for Holland-Bukit Timah GRC.
Under the stewardship of the seventh Principal, Ms. Chan Mee Leen, the school underwent a phased reconstruction which was completed in 2005. On 9 July 2005, the new campus was declared officially opened by Dr. Teo Ho Pin, Mayor of North-West District and Member of Parliament for Holland-Bukit Panjang GRC. In 2011, the school celebrated its 45th anniversary with an original musical.
On 15 December 2012, Mdm Tan Miao Ling was appointed the ninth Principal of CDSS, taking the mantle from Mr. Teoh Teik Hoe.
In late 2014, the school started her preparations for merger with Fajar Secondary School to become Fajar Secondary School, 励进中学, from 1 January 2016. On 21 November 2015, the school finally closed her doors with a fitting function “Celebrations 2015” where CDSS ex School Leaders, Pioneer Teachers, Senior Educators, ex-staff and ex-students attended. The function was graced by Ms Sim Ann, Senior Minister of State, Ministry of Culture, Community and Youth & Ministry of Finance and MP for Holland-Bukit Timah GRC.
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