Cities and towns have often developed infrastructure that enabled a variety of socio-economic interactions. Street networks within these urban settings provide key access to resources, neighborhoods, and cultural facilities. Studies on settlement scaling have also demonstrated that a variety of urban infrastructure and resources indicate clear population scaling relationships in both modern and ancient settings. This article presents an approach that investigates past street network centrality and its relationship to population scaling in urban contexts. Centrality results are compared statistically among different urban settings, which are categorized as orthogonal (i.e., planned) or self-organizing (i.e., organic) urban settings, with places having both characteristics classified as hybrid. Results demonstrate that street nodes have a power law relationship to urban area, where the number of nodes increases and node density decreases in a sub-linear manner for larger sites. Most median centrality values decrease in a negative sub-linear manner as sites are larger, with organic and hybrid urban sites' centrality being generally less and diminishing more rapidly than orthogonal settings. Diminishing centrality shows comparability to modern urban systems, where larger urban districts may restrict overall interaction due to increasing transport costs over wider areas. Centrality results indicate that scaling results have multiples of approximately ⅙ or ⅓ that are comparable to other urban and road infrastructure, suggesting a potential relationship between different infrastructure features and population in urban centers. The results have implications for archaeological settlements where urban street plans are incomplete or undetermined, as it allows forecasts to be made on past urban sites' street network centrality. Additionally, a tool to enable analysis of street networks and centrality is provided as part of the contribution.