Among organic compounds hydrocarbons are inexpensive and possibly the most abundant among natural resources. Developing strategies for selective functionalisation of inert hydrocarbon C–H bonds is one of the most ideal synthetic paths that a synthetic chemist could think of. This critical review focuses on the recent development of various directed and non-directed cycloalkylations leading to the formation of carbon–carbon (C–C) and carbon–heteroatom (C–X) bonds. Apart from various transition metal catalysed cycloalkylations, this review also covers various metal-free cycloalkylation processes.