In this work, a new procedure is demonstrated to retrieve the conservative and dissipative contributions to contact resonance atomic force microscopy (CR-AFM) measurements from the contact resonance frequency and resonance amplitude. By simultaneously tracking the CR-AFM frequency and amplitude during contact AFM scanning, the contact stiffness and damping were mapped with nanoscale resolution on copper (Cu) interconnects and low-k dielectric materials. A detailed surface mechanical characterization of the two materials and their interfaces was performed in terms of elastic moduli and contact damping coefficients by considering the system dynamics and included contact mechanics. Using Cu as a reference material, the CR-AFM measurements on the patterned structures showed a significant increase in the elastic modulus of the low-k dielectric material compared with that of a blanket pristine film. Such an increase in the elastic modulus suggests an enhancement in the densification of low-k dielectric films during patterning. In addition, the subsurface response of the materials was investigated in load-dependent CR-AFM point measurements and in this way a depth dimension was added to the common CR-AFM surface characterization. With the new proposed measurement procedure and analysis, the present investigation provides new insights into characterization of surface and subsurface mechanical responses of nanoscale structures and the integrity of their interfaces.