This review article describes the interaction of cyclodextrins (CDs) with polymer side chains as model systems for biological molecular recognition, focusing on the steric effect of the polymer chains, the effect of the conformation of the polymer main chain or competition with association of polymer side chains, and the effect of multi-site interaction. Some typical examples of stimuli-responsive systems, nanoparticles for drug delivery systems and macroscopic self-assembly based on the interaction of CDs with polymer side chains are also reviewed briefly.