Plastic films with microstructures are widely applied due to their outstanding performance in different fields. One of the applications is the manufacturing of flat panel displays for which conventional manufacturing methods using injection molding technology are inadequate. However, the rolling imprint method is an emerging technology that can overcome some shortcomings of traditional technologies in the fabrication of plastic films and flat panel displays. The quality of the precision roller has a direct impact on the accuracy of the microstructure pattern on the films. Research in this field currently focuses on the design and fabrication of precision rollers with little emphasis placed on the factors that affect the surface generation and measurement of the microstructure pattern. This chapter therefore presents the influence of machining factors on microstructure patterned surfaces on precision rollers by single point diamond turning, and introduces a model-based simulation system for the machining process.