Stiffness properties of interfacial engineering surfaces are of great importance to the dynamic performance of relevant mechanical systems. Normal contact stiffness and oil film stiffness of line contact problems are studied in this work analytically and numerically. The Hertzian contact theory and the Yang–Sun method are applied to predict the contact stiffness, while the empirical elastohydrodynamic lubrication (EHL) film thickness method and the complete numerical EHL model are used to predict the oil film stiffness. The numerical model mainly consists of the Reynolds equation; the film thickness equation, in which the regular surface roughness is taken into consideration; the force balance equation; and the viscosity-pressure equation. The effects of the normal load, rolling speed, regular surface waviness, and starved lubrication level on the oil film stiffness are investigated.