In the analysis of complex historical layering, studies on how to avoid theoretical analysis and use quantitative methods of display and analysis are scarce. Therefore, we used space syntax to fill this gap in historical layering analysis. We established a spatial digital model by combining the urban historical landscape theory with the space syntax analysis method. Then, we quantitatively analysed the streetscapes in the four historical periods of Macau and the value-related development of the city's economy, society, and culture. To this end, we used the theory of urban historical landscape to interpret the streetscape of Macau. We reviewed urban development under different spatial scales, which represent different states of historical layering. Changing ideological trends of construction have induced changes in the city, which have led to changes in the city style. The analysis considers the dimensions of space and time, and its results can guide the continued benign growth of the urban landscape and solve protection problems in practice. Meanwhile, the results of this work also indicate that the unique streetscape of Macau bred by the development of the city does not affect the newly constructed roads. The newly reclaimed areas and the streetscape of the new city are on the verge of homogeneity and cannot reflect the unique regional characteristics of Macau. Therefore, we used the historical map of Macau as a carrier, used space syntax to analyse the structure of Macau's streetscape, and explored the apparent characteristics and value associations carried by the streetscape of Macau under different historical slices. Our results can help retrieve the value of Macau's historical streetscape and devise a targeted protection strategy that can help pass on the historical streetscape of Macau to posterity.