A systematic resilience and flexibility analysis of future power systems to address the impacts of climate change and Renewable Energy penetration is becoming increasingly important, as it is expected to have a great effect on the demand and supply portfolios. Depending on the intrinsic characteristics of each power system, different aspects have to be considered in the analysis since this cannot be universal for all power systems. To highlight this, the paper presents two different case studies pertaining to the Great Britain and Cyprus networks respectively. Firstly, the resilience of the Great Britain transmission network to future demand and supply scenarios (2020, 2030 and 2050) is evaluated using a reduced version of the current Great Britain transmission network. Subsequently, the future flexibility requirements of the isolated network of Cyprus are appropriately benchmarked against future energy mix scenarios that involve conventional generation and renewable energy penetration.