Modeling of the complex tribological behavior of the elastomer parts is required when designing sliding seal applications. Friction, wear, and lubrication mechanisms of rubber-like materials differ from those in case of metals, ceramics, and rigid polymers; therefore, their modeling also requires other techniques. Tribological behavior of a sliding seal was investigated both experimentally and numerically. In the experimental setup, the counterpart of the seal was pressed and rubbed against the section of the seal in various lubrication conditions. The worn surface of the seal was inspected using white light profilometry. The test configuration was modeled by FEA. A wear algorithm (based on the linear wear theory) with an attached damage analysis was applied to the frictional contact simulation. The nonlinear and time dependent material behavior of the seal was also taken into account. The results of the tribological simulation (in which the internal friction and the effects of damage by rupture of the rubber material were considered) are in good agreement with the results of the surface inspections done on the worn seal specimens. The presented wear simulation technique of deactivating elements is suitable for modeling wear that is larger than the size of the elements in the FE mesh.