The use of synthesis gas (SYNGAS) from waste gasification has been pointed out as a key strategy to help the energy transition. However, SYNGAS’ low calorific power is considered a difficult obstacle to its technological use in internal combustion engines. To overcome this, a novel free-piston linear motor has been proposed to pave the way for the use of SYNGAS in the mobility sector. Surface texturing has vast potential to reduce friction losses in this system. This study utilizes a deterministic numerical model to investigate the mixed lubrication performance of a textured piston ring/cylinder liner conjunction in a free piston engine. The model considers the simultaneous solution of the lubrication and asperity contact problems at the roughness scale, including texturing features on the cylinder surface. The numerical model employs the Reynolds equation with mass-conserving cavitation to calculate the inter-asperity fluid pressure. The rough contact model utilizes the Hertz theory for elastic contact to calculate the contact pressure at each asperity between the piston liner surface and the admitted smooth and rigid ring surface. Surface texturing demonstrated remarkable effectiveness, particularly in the hydrodynamic lubrication regime, with a maximum friction reduction of 38.5% observed for an area coverage of 50%. This was accompanied by a notable shift in the transition from the boundary to the mixed lubrication regime. The textured surfaces exhibited consistent efficiency in reducing fluid pressure and shear stress as the coverage of the textured areas increased. The incorporation of dimples on these surfaces played a crucial role by augmenting the lubricant storage capacity while concurrently reducing the real shear and contact areas. This study offers valuable insights into the nuanced friction-reducing mechanisms of surface textures, illuminating their influence on the coefficient of friction and the formation of lubricant films across various lubrication regimes.