Abstract This study quantifies the possible impacts of urban heat-island countermeasures upon buildings’ energy use during summer in Tokyo metropolis. Considering the dependency of the buildings air temperature upon the local urban canopy structure, Tokyo urban canopies were classified in the city-block-scale using the sky-view factor (svf). Then, a multi-scale model system describing the interaction between buildings’ energy use and urban meteorological conditions was applied to each classified canopy. In terms of urban warming alleviation and cooling energy saving, simulations suggested that the reduction in the air-conditioning anthropogenic heat could be the most effective measure in office buildings’ canopies, and that vegetative fraction increase on the side walls of buildings in residential canopies. Both measures indicated daily and spatially averaged decreases in near-ground summer air temperature of 0.2–1.2 °C. The simulations also suggested these temperature decreases could result in the buildings’ cooling energy-savings of 4–40%, indicating remarkable savings in residential canopies. These temperature drops and energy savings tended to increase with the decrease of the svf of urban canopies.