Biomechanical studies are expanding across a variety of fields, from biomedicine to biomedical engineering. From the molecular to the system level, mechanical stimuli are crucial regulators of the development of organs and tissues, their growth and related processes such as remodelling, regeneration or disease. When dealing with cell mechanics, various experimental techniques have been developed to analyse the passive response of cells; however, cell variability and the extraction process, complex experimental procedures and different models and assumptions may affect the resulting mechanical properties. For these purposes, this review was aimed at collecting the available literature focused on experimental chondrocyte and chondron biomechanics with direct connection to their biochemical functions and activities, in order to point out important information regarding the planning of an experimental test or a comparison with the available results. In particular, this review highlighted (i) the most common experimental techniques used, (ii) the results and models adopted by different authors, (iii) a critical perspective on features that could affect the results and finally (iv) the quantification of structural and mechanical changes due to a degenerative pathology such as osteoarthritis.