Articular cartilage is a complex material where structure-function and biochemical composition are tightly regulated to provide a mechanically and biologically stable tissue capable of bearing large loads and providing friction-free motion in our joints. Recapitulating this complexity to produce tissue-engineered cartilage with matching functional integrity has proved challenging. In attempting to replicate tissue complexity, including zonal complexity for mechanical function and multiscale strain transfer, techniques for monitoring and analyzing the success (or failure) of these efforts in achieving functional integrity are also required. This chapter describes imaging modalities used to capture microstructural detail in native and tissue-engineered cartilage and provides an overview of articular cartilage structure and mechanical properties. An exploration of functional integrity for the purpose of cartilage tissue engineering and regeneration in a multiscale manner is given. A focus on multiscale mechanical properties and methods available in literature to capture this is described. Imaging tools used for capturing microstructural complexity and approaches for combining these with mechanical measurement are further explored, with insight into advantages and disadvantages. Specifically, in a hierarchical manner, studies exploring key structure-function aspects of cartilage are discussed: (i) fluid-solid interactions; (ii) fiber alignment for strain transfer; and (iii) its relationship to cell alignment; (iv) cell-scale mechanics linked to orientation, morphology, and deformation; and (v) the mechanical role of proteoglycan-rich microdomains. Prospects for further improvements and expansion to image-guided mechanical evaluation platforms in the cartilage and cartilage tissue-engineering field are offered.