In this second paper, the friction characteristics between roller and thin flexible web with different permeabilities is studied theoretically and experimentally. At first step, the standard test is carried out for three kinds of webs, PET (polyethylene terephthalate), coated paper and newsprint, for better understanding the friction characteristics between roller and web. Then, two types of power low model for the averaged contact pressure due to asperities of web and roller surfaces is presented, in which the unknown parameters involved in the models are determined by the inverse analysis to the standard test results of friction coefficient. Combining the contact pressure models developed here with the closed-form formula for air film thickness derived in the first paper, the prediction method of friction coefficient between web and roller is formulated. The air film thickness and friction coefficient are measured by changing the web width for three kinds of webs, and good agreements are obtained between the measured results and the predicted results. Moreover, based on these results, the effects of many design parameters on the friction characteristics are clarified.