Gold catalysis in the last two decade has witnessed remarkable improvements in terms of efficiency and scope of application in numerous organic reactions. In particular, the unique ability of gold catalysts to activate pi-bonds to effect various cycloaddition reactions has received significant attention. However, the catalytic application of gold in creating new opportunities for the regioselective cycloaddition reactions went largely unnoticed. Steric/electronic environment of substrates, ancillary ligand and reaction time seems to be some of the associated regio-directing factors in the gold-catalyzed cycloaddition reactions. Hence, in this review on gold catalyzed regioselective cycloaddition reactions, a complete update about the different types of gold-catalyzed cycloaddition of substrates like alkynes, alkenes, allenes, and ynamides along with the factors governing the selectivity is discussed. Applications towards natural product synthesis and tandem reactions to showcase the synthetic utility of such processes are also highlighted.