A facile method for controlling the self-assembly of supramolecular metallocycles on a highly oriented pyrolytic graphite (HOPG) surface is described. The process was demonstrated using 1,3,5-tris(10-carboxydecyloxy)benzene (TCDB), which self-assembles to form a stable monolayer with nanoscale cavities on HOPG, to template the deposition of supramolecular rectangles. Molecular distribution is controlled and monodispersion is achieved as the metallocycles self-organize into the cavities of the TCDB template.