The first building site of Gan Eng Seng School was located at No. 106 Telok Ayer Street between 1893 and 1941. A land grant was given by the British colonial government earlier to the philanthropist and founder, Mr Gan Eng Seng who paid S$5000 for the construction of the school building. Gan was credited for being the first local Chinese in Singapore to establish the free school in 1885 which emphasised bilingual education through his generous gift of property and funds until his demise. Most other schools of the time were established by missionary or communal organisations. The school was a two-storey wooden building and housed the school hall in the second storey. It started out as a primary school for boys and could accommodate up to 300 students. Governor H.E. Sir Clementi Smith officiated the school's Opening Ceremony on 4 April 1893. Mr Tan Keong Saik, a board trustee of the school briefly gave a history of the institution to the distinguished gathering. In 1908, a second school building was added to ease the overcrowding it faced with each passing year. The school was able to accommodate an almost twofold increase in students population of 641 afterwards. The school was finally abandoned in 1941 when the old section of the building was considered unsafe for use and it was housed temporarily in Sepoy Line Malay School in Park Road and Pearl's Hill School later.
Marking ceremony
On 30 August 1997, a marking ceremony was held at the junction of Telok Ayer Street and Cecil Street with twin structures jointly erected by the GESS Old Students' Association, the Singapore Gan Clan Association and the National Heritage Board near the historic site. Named In Dialogue, it consists of two granite miniature towers with plaques depicting the school's story and information on the founding site to symbolise the ongoing dialogue between the past and present generations of its students. About 600 past and present students returned to the site of the building which had been demolished and witnessed the marking ceremony. Distinguished alumnus like Dr. S. Vasoo, Member of Parliament for Tanjong Pagar GRC, Mr. Chua Kim Yeow, former Accountant General and Presidential Candidate, and retired Emeritus Professor Kiang Ai Kim of the National University of Singapore, were invited to grace the event. The school storyplaque reads: At present, the school is located at 1 Henderson Road with a student population of 1,300.
