Moving contact problems in a viscoelastic body with a rigid indentor are often seen in an industrial field. An evaluation of the time-temperature-dependent stress and strain behavior around a contact region is required in order to make clear the fundamental mechanism of the local fracture and wear on the contact surface of the viscoelastic body under moving loads with dry friction. No analyses have yet been published about the stress/strain of the viscoelastic moving contact problem with the dry friction using both an experimental and a numerical method. The authors discuss an experimental and a numerical model for the analysis of not only the viscoelastic stress and strain, but also deformations, taking into consideration the dry friction. An image-processing-aided photoviscoelastic technique is applied for analyzing the principal stress and strain behavior near the contact region. Also, a two-dimensional plane stress model which consists of a viscoelastic strip and a rigid sliding cylinder is adopted in a finite element analysis of the same problem. The time-dependent stress and strain and the coefficient of dry friction are successfully evaluated by experimental and numerical methods.