Monochloro-triazine β-cyclodextrin (MCT-βCD) was successfully utilized to modify the wool fabric structure. The modified wool exhibited better post-printing, using different dyestuffs, and outstanding antibacterial activities most probably due to the remarkable capacity of grafted βCD moieties to form guest–host inclusion complexes in addition to the positive role of wool's active sites. The following treatment sequence: pre-modification, post-printing, followed by after-treatment with Ag-NP's colloid or triclosan derivatives was investigated. The extent of improvement in the aforementioned properties is governed by the degree of pre-modification, type of dyestuff and extent of fixation, type of antibacterial agent, its mode of interaction and extent of loading onto the modified printed wool. The imparted antibacterial functionalities were retained, more than 75%, even after 15 washing cycles.