Viscoelastic contacts are present in countless industrial components including tires, dampers and rubber seals. The effective design of such components requires a full knowledge of viscoelastic contact mechanics in terms of stresses, strains and hysteric dissipation. To assess some of these issues, this paper describes a series of experiments on the contact area and penetration in a rolling contact between a nitrile rubber ball and a glass disk. The experimental results are compared with the theory proposed by Carbone and Putignano in [1] showing close agreement at low speeds. However, discrepancies arise at speeds above 100 mm/s because of the frictional heating. In order to evaluate this effect, the temperature of the sliding interface is measured for different rolling speeds using infrared microscopy. Thermal results showed that interfacial temperature remained constant at low rolling speeds before rising significantly when speeds above 100 mm/s were reached. These temperature effects are incorporated into the numerical simulations by means of an approximated approach, which corrects the viscoelastic modulus based on the mean measured temperature in the contact. The result of this approach is to extend the region of agreement between experimental and numerical agreement to higher speeds.