This paper broadens the analytical contours of Chinese migration by employing the paradigm of histoire croisée. By comparing three connected episodes within the nineteenth and twentieth centuries: (1) British expansionism; (2) Kuomintang activities and British migratory legislation; and (3) the interconnection of the slump in China's silk industry, the anti‐marriage movement, and the intertwinement of historiographies of China and Singapore – the entangled histories approach offers analytic purchase for which Chinese migration can be scrutinised with attention paid to the interpellations of historical contingencies and economic relations. The paper therefore analyses broader sociocultural and political patterns that inflect migratory flows, and considers the significance of how migratory historiography bears upon social memory of Chinese female migrants.