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Most previous studies clarify the interference effect between only two or three buildings, and very few assess the effect of a high-rise building within an urban block on its surrounding buildings. Accordingly, in this study, wind tunnel experiments were conducted on low-rise urban blocks having a high-rise building, and the wind pressure acting on the low-rise buildings was measured. For low-rise buildings located downwind of a high-rise building, an extremely low negative peak pressure was observed at the windward end of the roof at wind directions of approximately 30°. Further, a large-eddy simulation was applied to the flow field within an urban block, where extremely low negative pressure was observed. The strong negative pressure was generated because the detached flow at the windward corner of the high-rise building blew downward and struck the low-rise building located on the leeward side, and the flow became detached at the windward corner of the roof. The findings of this study indicate the importance of considering the wind-related damage to low-rise buildings caused by strong winds generated by high-rise buildings under extremely strong wind conditions. • Wind pressure on the low-rise buildings around a high-rise building was measured. • Negative pressure acting on the building roof behind a high-rise building was low. • Its negative peak value was extremely low at a wind direction of around 30°. • Wind flow that generated the strong negative pressure was analyzed by LES. [ABSTRACT FROM AUTHOR]