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.