We herein report the construction of homochiral, hierarchical self-assembled molecular networks (SAMNs) at the liquid/graphite interface using a single molecular building block, a chiral dehydrobenzo[12]annulene (cDBA) derivative with three chiral alkoxy and three hydroxy groups positioned in an alternating manner on the DBA core. The cDBA molecules form homochiral hierarchical SAMNs consisting of triangular clusters of several sizes, the size of which can be tuned by solvent polarity and solute concentration, reaching periodicities as large as 9.3 nm. We demonstrate the successful transmission of chirality information from the single molecular level to the hierarchical SAMN level, in a process that is mediated by dynamic self-sorting.