Cold forging is a metal forming that which uses localized compressive force at room temperature. During the cold forging process, the tool is subjected to extremely high loads and abrasive wear. Lubrication plays an important role in cold forging to improve product quality and tool life by preventing direct metallic contact. Surface roughness and residual stress also greatly affects the service life of a tool. In this study, variations in surface roughness, residual stress, and specimen deformation with the number of cold forging cycles were investigated under different forging conditions. Specimens that were made of heat-treated SKH51 (59–61 HRC), a high-speed tool steel with a polished working surface, were used. The specimens were subjected to an upsetting process. Compressive residual stress, surface roughness, and specimen deformation showed a positive relationship with the number of forging cycles up to a certain limit and became almost constant in most of the forging conditions. A larger change in residual stress and surface roughness was observed at the center of the specimens in all the forging conditions. The effect of the magnitude of the forging load on the above discussed parameters is large when compared to the effect of the lubrication conditions.