Gold (III)-N,N-dimethyldithiocarbamate [DMDT(Au)X2] complexes have recently gained increasing attention as potential anticancer agents because of their strong tumor cell growth–inhibitory effects, generally achieved by exploiting non-cisplatin-like mechanisms of action. The goal of our research work is to encapsulate the gold(III) dimethyldithiocarbamate complexes as anticancer with cucurbit[n]urils (CB[n = 5, 6]) by accurate calculations, to predict the inclusion complex formation of gold(III) species with cucurbiturils (CB[n = 5, 6]). The calculations were carried out just for the 1:1 stoichiometric complexes. Upon encapsulation, binding energy, thermodynamic parameters, structural parameters and electronic structures of complexes are investigated. The results of the thermodynamic calculations and the binding energy show that the inclusion process is exothermic and the CB[6]/[DMDT(Au)Br2] complex is more stable than other complexes. The final geometry of CB[n]/drugs indicates that the drugs were expelled from the cavity of CB[n]. NBO calculations reveal that the hydrogen bonding between CB[n] and drugs and electrostatic interactions are the major factors contributing to the overall stabilities of the complexes.