Vertical Greenery Systems (VGSs) are getting popular as a good strategy of introducing greenery into urban cities. Recent experimental studies have suggested that besides the aesthetic benefits, VGSs have the potential of providing thermal and energy benefits to the buildings. However, the current studies are limited a specific climate and shorter time durations. Therefore, this study aims at conducting a comprehensive analysis of thermal effects and annual cooling energy benefits of VGS in different climatic regions. The approach of the study was based on the building energy simulations with the EnergyPlus simulation program. The thermal effect of the VGS was quantified using a self-developed VGS model in our previous study. Whereas, the case study for the simulations was a single-story residential flat. The simulations have been carried out for four cities with different climates namely; Tropical moist climate – Kuala Lumpur, Malaysia, Dry climate – Abu Dhabi, UAE, Sub-tropical humid climate – Hong Kong and Mediterranean climate – Tarragona, Spain based on Koppen climate zone classification. The results depicted that cooling energy benefits are strongly weather dependent, resulting in attractive energy benefits for the climates with higher outdoor air temperatures and solar radiation. Hence, VGSs are likely to deliver significant cooling energy benefits during the summer.