A biomechanical investigation of the dynamic shear failure of the osteochondral region of immature, adolescent, and mature bovine cartilage bone laminates was performed. The osteochondral junction was loaded in pure shear under impact conditions through the cartilage layer only. The results indicate the adolescent tissue fails at a nominal shear stress of 2.0 MPa, whereas the immature and the mature tissues fail at 3.8 MPa and 2.6 MPa, respectively. The adolescent tissue had a significant reduction in the fracture toughness of its osteochondral junction compared with that of the immature or mature tissues. The fracture toughness, describing the energy required to initiate and propagate a crack to failure, was 3.6 kN/m, 2.3 kN/m, and 10.2 kN/m for the immature, adolescent, and mature bovine tissues, respectively. This significant reduction associated with the adolescent osteochondral junction is explained in terms of the structural changes occurring within this important anchoring region during maturation. These findings question the wisdom of subjecting the adolescent joint to high levels and rates of loading.