Chong Boon Secondary School accepted its first batch of students in December 1993, taking over Anderson Secondary School's old building. In total, there were 483 Secondary One students in 13 classes and 23 staff then. Mrs Cecilia Lee was appointed Principal.
1995
In the second year, the enrolment grew to 772 students with 35 staff. The first Prize Presentation Day was held.
1996
Official Opening was held. The Concert Band showcased its first concert performance ‘Metier I’.
1997
The school achieved a Silver award for the ‘Concert Bands’ category in the Singapore Youth Festival (SYF) Central Judging Competition. The school achieved a Silver award for the ‘Contemporary Chinese Dance’ category in the Singapore Youth Festival (SYF) Central Judging Competition. The Concert Band showcased its first outdoor performance ‘Metier II’ at the Victoria Concert Hall.
1998
In December, Mrs Cecilia Lee was appointed Principal of Junyuan Secondary School and Mdm Sun Huey Min took over as Principal.
1999
The school was awarded a Bronze medal for the ‘Concert Bands’ category in the Singapore Youth Festival (SYF) Central Judging Competition. The school was awarded a Bronze medal for the ‘Contemporary Chinese Dance’ category in the Singapore Youth Festival (SYF) Central Judging Competition. The school also came first in the National Inter-School Yachting Championship. The school organised the N4 Cluster Parents' Seminar at the Methodist Girls' School. CBSS webpage was launched.
2000
The school vision, ‘A Thinking & Gracious Citizen’, was formulated. In April, the school's rebuilding project began on the combined site of CBSS and Chong Li Primary School site. The sailing team won Zonal and National Colours Awards as well as taking part in international events.
2001
The school was awarded a Silver medal for the ‘Concert Bands’ category in the Singapore Youth Festival (SYF) Central Judging Competition. The school was awarded a Silver medal for the ‘Contemporary Chinese Dance’ category in the Singapore Youth Festival (SYF) Central Judging Competition. The school’s Concert Band was invited to perform at the Istana on Labour Day. The demolition of the CBSS old school building began in December 2001.
2002
In March, the school's Core Values: Perseverance, Respect, Integrity, Dedication to the Nation and Excellence (PRIDE) were formulated. The school embarked on a new beginning with the shift to its new premises. The 1st Student Councillors' Investiture Ceremony was held.
2003
The school achieved value-added results for the Express Stream in the GCE 'O' Level Examinations. The school received a Gold award for the ‘Contemporary Chinese Dance’ category in the Singapore Youth Festival (SYF) Central Judging Competition. The school received a Silver award for the ‘Concert Bands’ category in the Singapore Youth Festival (SYF) Central Judging Competition. The school received a Bronze award for the ‘Choir’ category in the Singapore Youth Festival (SYF) Central Judging Competition.
2004
The official completion of PRIME was followed by the Official Opening of the new School Building and its 10th anniversary celebrations by Mr Chan Soo Sen, Minister of State for Education & Community Development and Sports. Down Memory Lane was established, with the aim to capture and showcase the school's history for the past 10 years, incorporating I&E, Social Integration and a Holistic Education. The school embarked on creating a learner-centred environment to bring learning beyond the classroom.
In December, Mdm Sun Huey Min, the school's second Principal, was appointed Assistance Director, Staff Training and Development, and Mrs Sarapathy Menon took over as Principal.
2005
Doing It Differently was an attitude the school had embraced to engage the entire school to reflect on all that was happening in school, pondering on the purpose and value underlying these processes and offering suggestions to add value to them. For example, students were encouraged to seriously mull over the need for an enhanced school tone and discipline and to present their views on the desired outcomes. Suggestions by students for school improvement were welcomed and rationale for decisions were discussed to help them appreciate the value and respect for collective responsibility. The school received a GOLD award for the ‘Concert Bands’ category in the Singapore Youth Festival (SYF) Central Judging Competition.
2005 started off with the student leaders from Sec 2 to Sec 5 getting together to plan and organise the Sec One Orientation. The programme, called ‘The Metamorphosis’, was so successful that they felt confident enough to take on greater responsibilities and had gone on to be key players in organising this year’s school’s Cross Country, the Track and Field event and Total Defence Day. One other initiative undertaken by the IT Club was the ‘Computer Literacy Course’ for Parents. Sec 3 and 4 pupils prepared course materials and conducted the course and now they have plans to impart computer skills to their junior schoolmates.
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