Surface texturing is a promising way to expand the hydrodynamic lubrication regime and thereby modify the tribological properties of sliding surfaces. Spiral-groove textures in particular have attracted much attention over the past several decades because they produce a thicker lubrication film in the gap. However, no research has been reported on the effect of periodic texturing with a several 100 nm depth on hydrodynamic performance in submicrometer clearance with surface roughness. The purpose of the study reported here was to investigate the effect of such nanotexturing on hydrodynamic performance. This was done by conducting ring-on-disk friction tests, focusing on the existence of surface roughness in the narrow clearance. The samples were rings with various degrees of surface roughness and disks with spiral-groove textures produced by femtosecond laser processing. The friction coefficients experimentally obtained were plotted as a Stribeck curve and compared with a theoretical one calculated using a Reynolds equation formulated from two physical models, the Patir–Cheng average flow model and a sinusoidal wave model. The results showed that surface roughness did not affect the friction coefficient in the hydrodynamic lubrication regime. However, the hydrodynamic lubrication regime gradually shrank with an increase in surface roughness, and mild transitions to the mixed lubrication regime were observed at higher rotational speeds. The minimum clearances reached at the transition speed were almost the same, about 200–300 nm, for all experiments regardless of surface roughness.