The creation of polymeric materials that self-strengthen in response to a mechanical force is an important objective in the field of polymer chemistry. Here, the mechanochemical strengthening of cross-linked elastomers using macrocyclic mechanophores that contain a dynamic covalent disulfide bond is reported. Cross-linked poly(hexyl methacrylate) (CPHMA) polymers with macrocyclic mechanophores inserted at the cross-linking points were synthesized via free radical polymerization. Tensile and swelling tests showed that the addition of the macrocyclic mechanophores to the CPHMA polymers successfully impart them with self-strengthening functionality following compression, without the need for any additives such as monomers and modifiers, or any other stimuli.