Mechanochemistry has been utilized in the synthesis of several macrocycles, inducing covalent self-assembly of uniformly structured monomers. As mechanosynthesis enables overcoming the solubility barriers and promotes reactions between compounds with drastic polarity differences, its potential can be exploited even further. To the best of our knowledge, there have been no reports describing solid-state formation of oligomeric macrocycles from mixtures of various monomers. Formation of chiral chimeric HCs via self-assembly in the solid state could pave the way to novel synthetic approaches, unlocking access to versatile applications.