Methodological studies on the transformations of vinylidene cyclopropanes (VDCPs) have been substantially developed in the past few decades, and significant progress has been achieved in visible light-mediated, non-metal-related, and transition metal-catalyzed processes. In particular, when reactive functional groups are introduced into the backbone of VDCPs, a variety of cascade or sequential transformations can take place to produce more complex cyclic or polycyclic compounds. This review describes the recent advancements in this field.