The roll-to-roll (R2R) fabrication method to make micro-scale pillar arrays for biomimetic functionalization of surfaces is presented. Inspired by the micro-structure of plants in nature, a surface with a synthetic micro-scale pillar array is fabricated via maskless photolithography. After the surface is SAM (self-assembled monolayer) coated with trichlorosilane in a vacuum desiccator, it displays a hydrophobic property even in R2R replicas of original substrate, whose properties are further characterized using various pitches and diameters. In order to perform a comparison between the original micro-pattern and its replicas, surface morphology was analyzed using scanning electron microscopy and wetting characteristics were measured via a contact angle measurement tool with a $10{mu}L$ water droplet. Efficient roll-to-roll imprinting for a biomimetic functionalized surface has the potential for use in many fields ranging from water repelling and self-cleaning to microfluidic chips.