The behaviour of axially loaded prestressed stayed columns is a commonly studied area. Despite the fact that load eccentricity in columns is commonplace in practice, the amount of investigation into these systems under eccentric loading is limited. This study employed finite element analysis to investigate the interactive post-buckling behaviour of prestressed stayed columns. Critical imperfection combination with respect to the load carrying capacity was established and a comparison of a planar and a three-dimensional model was carried out to investigate key differences in the models. In this work, it has been shown that the load carrying capacity of eccentrically loaded columns can be significantly reduced when buckling in interactive mode is observed. Furthermore, it was established that increase in eccentricity results in a decrease in load carrying capacity of columns for both planar and three-dimensional models. However, a major difference between the models is the twisting effect exhibited in the three-dimensional model under out-of-plane eccentric loading. This work highlights the importance of carefully designing prestressed stayed columns’ connections to minimise loading eccentricity as it has been shown that the benefit of employing these systems over unstayed columns reduces with increasing load eccentricity.