As a pivotal city in the Guangdong-Hong Kong-Macao Greater Bay Area (referred to as the Greater Bay Area hereinafter), Macao is renowned for its development history that spans several centuries. While existing studies approach Macao’s urban development from multiple perspectives, such as political system, urban space, urban construction, and planning concept, they don’t yet adequately underscore the fundamental role of the Portuguese urban planning system in Macao’s long-term development. Employing the tool of theme river chart, this study visualizes Macao’s urban development from 1845 to 2022 into five periods with a distinctive feature respectively, i.e., the implementation of colonial rules, the consolidation of colonial rules, the development of a neutral zone, the development of a high-degree autonomy, and the development under the “One Country, Two Systems” policy. It finds that Macao’s urban development in the modern and contemporary times is synchronously shaped by six key dynamics. They are demographic changes reflecting institutional fluctuations, land expansions mirroring the evolution of urban texture, legal norms ensuring orderly development, shifts of urban development goals from individual buildings to regional integration, requirements for improving living quality, and forward-looking planning in response to actual demands. It concludes that Macao’s urban development in the modern and contemporary times demonstrates some notable strengths, such as resilience throughout fluctuations, prevention of proactive conflicts, refinement of regulatory frameworks, emphasis on development constraints, management of fine-tuned demands, and phasing of forward-looking planning, which can offer valuable historical insights, development paradigms, and future prospective for other cities.