As cities grow, their spatial configurations may undergo some changes over time. This study attempted to examine the impact of the changes that occurred to the spatial configuration of the historical district of Shiraz on perceived anti-social behavior (ASB). Space syntax techniques were used to assess whether they can explain the extent to which perceived levels of anti-social behavior were impacted by these changes. Historical and present maps of the city were obtained and spatially analyzed using DepthmapX. The perceived ASB was assessed using seven groups of factors identified from the existing literature. These factors were evaluated using questionnaires distributed to long-term residents living in the area; in total, 98 respondents responded to the questions using a five-point Likert scale. Findings demonstrated that the perceived ASB was concentrated along highly integrated street segments. The unplanned transformations also introduced a large number of fragmented street segments, making it a challenge to connect the inner streets to the rest of the city. The spatial metrics used in this study could provide a useful tool for planners, urban designers, and policymakers, who can thereby measure the impact of proposed city modifications on social behavior and the residents’ quality of life.