The prevalence of osteoarthritis is on the rise, and an effective treatment for cartilage defects is still being sought. Cartilage tissue in vivo encompasses complex structures and composition, both of which influence cells and many properties of the native cartilage. The extracellular matrix structure and components provides both morphological cues and the necessary signals to promote cell functions including metabolism, proliferation, and differentiation. In the present study, cryo-printing and electrospinning were combined to produce multizone scaffolds that consist of three distinctive zones. These scaffolds successfully mimic the collagen fiber orientation of the native cartilage. Moreover, in vitro analysis of chondrocyte-seeded scaffolds demonstrated the ability of multizone scaffolds to support long-term chondrocyte attachment and survival over a 5 week culture period. Moreover, multizone scaffolds were found to regulate the expression of key genes in comparison to the controls and allowed the detection of sulfated glycosaminoglycan. Evaluation of the compressive properties revealed that the multizone scaffolds possess more suitable mechanical properties, for the native cartilage, in comparison to the electrospun and phase-separated controls. Multizone scaffolds provide viable initial platforms that capture the complex structure and compressive properties of the native cartilage. They also maintain chondrocyte phenotype and function, highlighting their potential in cartilage tissue engineering applications.