Cyclic dipeptides (CDPs) are heterocyclic 2,5-diketopiperazines with exceptional structural rigidity, enzymatic stability, and biological activity, exhibiting a substantial tendency to take part in intermolecular interactions. Strong intermolecular interactions driven by unique hydrogen bonding patterns render CDPs with a high propensity to undergo molecular self-assembly. In this Review, the aim is to provide a comprehensive summary of design strategies used to engineer the molecular self-assembly of CDPs into functional nano- and micro-architectures and molecular gels with potential applications in biomedical and materials engineering fields.