: To investigate the underlying mechanism of the effects of surface texturing on lubricated sliding friction in the metal forming operation, an in-situ observation system using transparent silica glass dies and a high speed recording camera was newly developed. To correlate the dimensional parameters of micro-dimple textured structures and tribological properties in the metal forming operation, the in-situ observation was performed during bending with the ironing process of the stainless steel sheet with a thickness of 0.1 mm. The lubrication behavior were compared between the different lubricant viscosities and the micro-dimple textures with different diameters of 10 µm, 50 µm, 100 µm fabricated by using femto-/pico-second laser processing. As a result, the textured die with dimple diameters of 10 µm and 50 µm showed the lubricant flow transferred from one to the other dimples owing to the lubricant reservoir effect, while that of 100 µm indicated the less supply of the lubricant. However, the textured die with a dimple diameter of 10 µm demonstrated higher ironing force than that of 50 µm, due to the severe adhesion of work materials inside the dimple structures. Based on these experimental findings, the dimple size dependencies on lubricant reservoirs effects and the generation of the hydrodynamic pressure were discussed by correlating with the in-situ observation results, a fluid-flow analysis and a laminar two-phase flow analysis using the finite element method.