Air entrainment of a winding roll with a nip roller was studied numerically. The amount of air entrainment between two rotating rollers was obtained by solving lubrication equation, Reynolds equation, which neglect the existence of a web. However, the numerical model of this study included the web existence, therefore it considered the two lubricating air films between a winding roll and a web and also between a nip roller and the web. The pressure profiles and gap profiles of the two films were obtained by solving lubrication equation for the two air films and force balance equation of the web. Ballooning phenomenon was examined in terms of nip force, wrap angle, web stiffness, web speed, and web tension. This ballooning phenomenon caused by the back flow of the air film blocked by the nip roller. Air entrainment of the two numerical models was compared.