The street was constructed in 1837 and was initially named Church Street after Thomas Church, who became a resident councillor that same year. A survey of this street was done by J.T. Thomson, and it is very likely that he used Church's name for the street due to the close working relationship between the two of them. The street name was renamed to its present name by the Municipal Council in 1858 to commemorate the Duke of Wellington's victory over the French in 1815, the Battle of Waterloo. Formerly a one-way street, the street has been converted to a two-way street and the northern end of the street has been converted into a pedestrian mall to ease the problem of traffic jams, as well as the crowd at Kwan Im Thong Hood Co Temple, which was most packed during the weekends and public holidays. The street, which previously extended to Stamford Road, has been shortened after the construction of the Singapore Management University's city campus and the MRT station.
There are several well-known landmarks, including the Kwan Im Thong Hood Cho Temple, Maghain Aboth Synagogue, Sculpture Square, and Sri Krishnan Temple. The Maghain Aboth Synagogue is the oldest synagogue in Singapore and was built by the local Jewish community in 1878.
The Tamils call the street krishmen kovil sadakku or "Street of the Krishnan Temple", where the Sri Krishnan Temple is located next to the Kwan Im Thong Hood Cho Temple. The street is known as mang ku lu chai tng koi in Hokkien, which means the street in Bencoolen where the vegetarian hall is.
Waterloo Street is parallel to North Bridge Road, Victoria Street, and Queen Street (in sequence); these were previously the major roads to the city. As the road names were too difficult to pronounce for the locals, they simply called them Toa Beh Lo, Tzee Beh Lo, and Sa Beh Lo which means "the big (first) road", "the second road", "the third road". The Hokkiens and Teochews call Waterloo Street si beh lo which simply means "the fourth road".
- OG Albert Complex
- The Bencoolen
- Fu Lu Shou Complex
- Albert Centre and Cheng Yan Court
- Kwan Im Thong Hood Cho Temple
- Sri Krishnan Temple
- Fortune Centre
- Sculpture Square (Former Middle Road Church, which is now known as Kampong Kapor Methodist Church)
- Maghain Aboth Synagogue
- Singapore Art Museum
- Plaza by the Park
- Victor R Savage, Brenda S A Yeoh (2004), Toponymics – A Study of Singapore's Street Names, Easter University Press.
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