Place names do not simply refer to physical locations. They are linguistic symbols full of connotative meaning, carrying a range of cognitive, social, historical, cultural, and ideological significance. Naming (or renaming) has been a key aspect of the colonisation process, through which the colonisers have used language to assert their power over the colonised. Singapore has a very rich history, which includes pre-colonial, colonial, and post-colonial periods. This paper examines selected toponymic changes in Singapore that occurred against the backdrop of colonialism. Given Singapore’s colonial past, as well as its multilingual and multicultural context, the paper aims to provide a thorough and insightful documentation of selected toponymic changes, while uncovering the underlying reasons that motivated them. Four place names (as they are currently known) are investigated in this paper: Jalan Besar, Havelock Road, Middle Road, and the Padang. An analysis of historical data revealed that toponymic changes associated with these places during colonial rule mostly reflected the asymmetrical power relationship between the colonisers and the colonised. The paper also highlights the historical processes in which naming deviated from such expectations.