The contact resistance of field effect transistors based on pentacene and parylene has been investigated by experimental and numerical analysis. The device simulation was performed using finite element two-dimensional driftdiffusion simulation taking into account field-dependent mobility, interface/bulk trap states and fixed charge density at the organic/insulator interface. The width-normalized contact resistance extracted from simulation which included an interface dipole layer between the gold source/drain electrodes and pentacene was 91 k cm. However, contact resistance extracted from the simulation, without consideration of interface dipole was 52.4 k cm, which is about half of the experimentally extracted 108 k cm. This indicates that interface dipoles are critical effects which degrade performances of organic field effect transistors by increasing the contact resistance. Using numerical calculations and circuit simulations, we have predicted a 1 MHz switching frequency for a 1 µm channel length transistor without dipole interface between gold and pentacene. The transistor with dipole interface is predicted, via the same methods, to exhibit an operating frequency of less than 0.5 MHz.