Attachment of β-cyclodextrin (β-CD) molecules on cotton textile provides hosting cavities that can include a large variety of guest molecules for specific functionality. Five different new and existing techniques were evaluated for connecting β-CD and its derivatives to cotton surface. A comparison has been made in terms of maximum attachment of β-CD on cotton surface. Novel chemical based crosslinking with homo-bi-functional reactive dye (C.I. reactive black 5) and grafting with reactive monochlorotriazinyl-β-cyclodextrin show maximum attachment to cotton surface. Innovative, enzymatic coupling of especially synthesized 6-monodeoxy-6-mono(N-tyrosinyl)-β-cyclodextrin was performed on cotton textile surface. Enzymatic coupling was also carried out in a homogeneous system and attachment confirmed by UV–vis spectroscopy. This tyrosinase mediated coupling is low temperature and very specific technique. A phenolphthalein based analytical method was partially modified to reliably measure the amount of attached β-CD on cotton surface. Atomic force microscopy and scanning electron microscopy techniques were used for surface characterization of the treated and untreated cotton surfaces. Alteration in surface topography has been observed for β-CD treated samples.