Owing to the selective recognition ability, exceptional biocompatibility, water solubility, non-toxicity, economically inexpensive, commercial availability, and easy functionalization, cyclodextrins (CDs) act as the main building blocks for the creation of beautifully simple yet much effective supramolecular architectures of fundamental interest. Over the past few decades, CDs have engrossed a noteworthy interest in the scientific community because of their usage in the development of chemical sensors via molecular recognition phenomenon. Bearing the delightful sensing capability of CDs in mind, herewith, we envisioned to disclose the recent developments in the sensing of diverse biologically significant small molecules by CDs through colorimetric, fluorescence, electrochemical, and potentiometric response. Sensing events and corresponding distinguishing optical features in cyclodextrin-based monomers, dimers, clusters, and nano-assemblies have been elaborated in detail. The authors are of the opinion that this chapter will offer new dimensions to supramolecular sensors in general and CDs-based sensors in particular.