The goal of this research is to develop adhesive rubber micro structures with micro suction cups, which realize new functions such as flexible-fitting and anisotropic adhesion. They can be applied to various robot mechanisms such as wall-climbing robots and robot hands, etc. Through micro rubber molding methods, we have successfully fabricated the micro structured rubber sheet of 10mm^2 in area, which consists of 144 suction cups of 500μm in diameter. Making the experiments of this sheet, we show experimentally a relationship between the integration of suction cups and flexible-fitting adhesion. Addtionally, the nonsymmetrically-shaped suction cup has been designed using nonlinear finite element method and the model with 10mm in diameter is fabricated. The experimental results show the possibility of this new functional rubber sheet, which can be attached and removed by changing loading direction.