The roughness retention ability of the work roll surface during the cold rolling process is of great significance, especially in the production of the high-quality rolling section. Laser shock peening (LSP) is an advanced and effective surface treatment technique to improve the fatigue life, wear resistance, and other mechanical characteristics of metal components. Current studies commonly examined the reinforcement effect of single and multiple LSP treatments on Cr5 steel samples through XRD analysis, hardness testing, and residual stress measurements of different parameters. In addition, the abrasion test is widely conducted to determine the wear resistance. Compared to unprocessed samples, LSP could promote grain refinement and thus significantly increase the hardness and residual stress. Furthermore, the slight decrease in surface roughness shows that LSP treatment is an effective approach to slowing down the roughness decline rate and prolonging the roller service life. It is also found that multiple LSP impacts could remarkably improve the surface roughness retention of Cr5 steel, in which the optimal laser power density was around 23 GW/cm2.