Singapore's topography has been heavily transformed by industrialization and urbanization processes. To investigate topographic changes and evaluate soil mass flows, historical topographic maps of 1924 and 2012 were employed, and basic topographic features were vectorized. Digital elevation models (DEMs) for the two years were reconstructed based on vector features. Corresponding slope maps, a surface difference map and a scatter plot of elevation changes were generated and used to quantify and categorize the nature of the topographic transformation. The surface difference map is aggregated into five main categories of changes: (1) areas without significant height changes, (2) lowered-down areas where hill ranges were cut down, (3) raised-up areas where valleys and swamps were filled in, (4) reclaimed areas from the sea, and (5) new water-covered areas. Considering spatial proximity and configurations of different types of changes, topographic transformation can be differentiated as either creating inland flat areas or reclaiming new land from the sea. Typical topographic changes are discussed in the context of Singapore's urbanization processes. The two slope maps and elevation histograms show that generally, the topographic surface of Singapore has become flatter and lower since 1924. More than 89% of height changes have happened within a range of 20m and 95% have been below 40m. Because of differences in land surveying and map drawing methods, uncertainties and inaccuracies inherent in the 1924 topographic maps are discussed in detail. In this work, a modified version of a traditional scatter plot is used to present height transformation patterns intuitively. This method of deriving categorical maps of topographical changes from a surface difference map can be used in similar studies to qualitatively interpret transformation. Slope maps and histograms were also used jointly to reveal additional patterns of topographic change.