Abstract: As a core city in the Guangdong-Hong Kong-Macao Greater Bay Area, Macao carries a rich urban history spanning several centuries. Existing scholarship has examined Macao's urban development from multiple perspectives, including political institutions, urban space, construction, and planning, yet it has not sufficiently highlighted the foundational role played by the transplantation of the Portuguese urban planning system into Macao. Using the theme-river visualization tool, this paper maps the trajectory of Macao's urban development from 1845 to 2022 and divides it into five periods: the period of implementing colonial rule, the period of consolidating colonial rule, the neutral-zone development period, the period of high regional autonomy, and the new era of "One Country, Two Systems." The study finds that Macao's modern and contemporary urban development has been driven by six interrelated logics: population change as a reflection of political fluctuation; land expansion as a record of urban fabric evolution; legal norms as safeguards for orderly development; urban objectives shifting from individual buildings to regional integration; the continuous improvement of existing environmental quality; and forward-looking planning grounded in the anticipation of demand. The paper concludes that Macao's urban development demonstrates several strengths, including breakthroughs generated by volatility, the prevention of deferred and entrenched conflicts, regulatory guidance through improved laws, attention to development constraints, refined demand orientation, and phased prospective planning. These experiences provide valuable historical insights, development paradigms, and future perspectives for analyzing the development logic of other cities.