This paper describes the experimental methodology used to study the contact mechanics of a rigid, rough surface and a compliant, nominally flat surface using digital image correlation (DIC). The rough surface was produced by 3-D printing PMMA and the flat surface was produced with transparent PDMS (silicone rubber). The deformation of the speckled top surface (contact) of the PDMS was measured via DIC viewed through the transparent media. Four different PDMS formulations with moduli ranging from 64 to 2120 kPa were used in the experiment program to cover a wide range of modulus normalized loads. The deformation of the contact surface and depth of penetration versus normalized load were measured. The results were overlaid with previous measurements of contact area and complemented them extremely well. Additionally, it was shown that scaling laws associated with such contact mechanics problems extend many length scales.