Porous microspheres from discotic tripeptides have been investigated as potential candidates for drug delivery vehicles. The C3 symmetric discotic tripeptide adopts a supramolecular helical column structure by three fold intermolecular hydrogen bonding interactions as well as face to face π-π stacking interactions. But the C2 symmetric discotic tripeptide adopts a supramolecular dimer like structure by six-fold intermolecular hydrogen bonding interactions and face to face π-π stacking interactions. Field emission scanning electron microscopy (FE-SEM) revealed that the C3 symmetric discotic tripeptide exhibits bird nest-like porous microsphere morphology formed by the assembly of the individual columns. However the C2 symmetric discotic tripeptide forms round clay pitcher like porous microspheres. These porous microspheres have been used as potential carriers for the sustained release of a bacteriostatic antibiotic sulfamethoxazole. The spectroscopic studies as well as the growth inhibition of E. coli reveal that the round clay pitcher-like porous microspheres are more efficient than the bird nest-like porous microspheres for the sustained release of drugs. The report highlights the importance of the self-assembly pattern for the fabrication of advanced functional materials.