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Prior to 1874
Prior to 1874, in response to a need to provide the opportunity of learning English through the medium of the mother tongue of the various races, two schools were built in Singapore, one at Cross Street and other at Kampong Glam.

Establishment of School
As the numbers in the school at Cross Street grew, there was a plan to establish a training school to meet demands. But for some unknown reasons, this plan did not materialise. A new school, Outram Road School, built at Outram Road, was formally opened by the Governor of Singapore, Sir John Anderson on 26th February 1906. By Gazette notification in 1939 the word "Road" was deleted and the school was known as Outram School.

Early History From 1906
Outram School functioned as a Primary School. Acting as feeder school, Pearl's Hill Standard One proceeded to Standard Two at Outram. Likewise, Outram was the feeder school to Raffles Institution. The working arrangement between Pearl's Hill School and Outram School continued up to January 1953 whereas the working agreement between Outram and Raffles Institution ceased with the fall of Singapore in February 1942. After the war, Outram boys competed with other Government Primary School pupils in securing places in Government Secondary Schools.

Lost Records (1906 to 1942)
Under the orders of the Education Department, Mr SG Mohamed Ghows, who was Outram's Principal in 1941, sent all Outram School's records to the Pasir Panjang English School for safe keeping. Subsequently, this school suffered a direct hit during the Japanese War and with it went all Outram's past records, from 1906 to 1942.

Conversion into a Secondary School in 1954
O n 1st January 1954, Outram ceased to be a purely Primary School and was converted to a four year Secondary Commercial School with a four year secondary school course leading to the School Certificate of Commercial Education of the London Chamber of Commerce. With the conversion, the school motto was changed from "ON TO SUCCESS" to "LABOR OMNIA VINCIT" – Labour Conquers All. The School's crest was also changed.

Significant Events from 1954 to Present
1957 - The first group of candidates took the London Chamber of Commerce School Certificate of Commercial Education Examination which became the Secondary School Leaving Examination

1958 - Girls were admitted to the school for the first time

1961 - The school was renamed Outram Secondary School

1964 - The first group of Secondary 4 students took the Examination for the Cambridge Overseas School Certificate and the school leavers no longer took the London Chamber of Commerce Examination

1965 - The Old Outramians' Association was formed

1968 - The school moved to its premises at York Hill, off Chin Swee Road. The school site at Outram Road was demolished in November/December 1968 to make way for Urban Renewal and Development. The Outram Secondary School Advisory Committee was formed

1969 - The school was converted to a multi-purpose Secondary School offering academic education with commercial bias at Upper Secondary level. However, in recent years, this emphasis has changed to the Sciences and the Humanities. The Higher School Certificate in Commercial Education was introduced for the first time in Singapore. Outram was the only school in Singapore with Commercial Education up to H.S.C. Level till 1973.

1976 - The Foundation Stone of the Swimming Pool Complex was laid by the late Mr Hon Sui Sen, Minister for Finance and Member of Parliament for Havelock.

1977 - The Swimming Pool Complex was completed and officially opened by Mr Hon Sui Sen on 15th October, 1977

1979 - A three year Pre-University course was introduced. A new School Advisory Committee comprising entirely of old boys and ex-teachers was formed

1983 - The Ministry of Education piloted the School Executive Committees in some schools, one of which was Outram.

1988 - The pilot Outram School Executive Committee was taken off by the Ministry of Education.

1994 - Outram moved to its site at 10, Winstedt Road in June to make way for the redevelopment of a new premises at York Hill.

1996 - Outram celebrated its 90th anniversary 1998 - Outram moved back to the present site in June.

1999 - Opening Ceremony of the new premises at York Hill on 28 August

2006 - Outram Centennial Celebrations and Launch of the Outram Centennial Commemorative Book "Labor Conquers All - 100 years of Outram Secondary School."

2007 - Launch of South 4 Centre of Excellence for Business and Enterprise.

2007 - First school in Singapore to offer GCE 'O' Level Business Studies as one of the 'O' Level Subjects

2007 - Niche Programme School for Rock climbing

2008 - One of two secondary schools in Singapore to offer "introduction to Enterprise Development" as an Applied Subject in collaboration with Singapore Polytechnic, School of Business

2016 - Outram celebrated its 110th anniversary with a Homecoming Carnival and a Homecoming Dinner and launched its 110th Anniversary Commemorative Book "Reminisce, Re-live, Reconnect"

2016 - Opening Ceremony of the new Indoor Sports Hall (ISH) 

2018 - The school began its re-envisioning exercise in response to the changing educational needs in the new century. Together with the school staff, the following changes were made:

  • New vision: Lifelong Learners . Innovative Leaders . Caring Contributors