During the ongoing evolution of energy systems toward increasingly flexible, resilient, and digitalized distribution systems, many issues need to be developed. In general, a holistic multi-level systemic view is required on the future enabling technologies, control and management methods, operation and planning principles, regulation as well as market and business models. Increasing integration of intermittent renewable generation and electric vehicles, as well as industry electrification during the evolution, requires a huge amount of flexibility services at multiple time scales and from different voltage levels, resources, and sectors. Active use of distribution network-connected flexible energy resources for flexibility services provision through new marketplaces will also be needed. Therefore, increased collaboration between system operators in operation and planning of the future power system will also become essential during the evolution. In addition, use of integrated cyber-secure, resilient, cost-efficient, and advanced communication technologies and solutions will be of key importance. This paper describes a potential three-stage evolution path toward fully flexible, resilient, and digitalized electricity distribution networks. A special focus of this paper is the evolution and development of adaptive control and management methods as well as compatible collaborative market schemes that can enable the improved provision of flexibility services by distribution network-connected flexible energy resources for local (distribution system operator) and system-wide (transmission system operator) needs.