This article provides an overview of the available literature data on direct CH functionalization reactions used for introducing alkenyl and alkynyl groups into heterocyclic systems. The information has been systematized according to the type of the experimental procedure and the nature of the (hetero)arene moiety. The time period covered in this review starts from the first example (according to our knowledge) when ethyne moiety was introduced into aza-heterocycles using СН functionalization in 1961, until the present time. A total of 100 references have been provided.