The synthesis of a series of copolymers via ring-opening metathesis polymerization (ROMP) containing pendent trimethylsilyl-protected alkyne functional groups is described. Deprotection of the protected ynes yields copolymers with free alkyne functionality that can be utilized as a reactive handle for thiol–yne (TYC) and Cu-catalyzed alkyne–azide coupling (CuAAC) either independently or together.