In a web winding process, the contact roll plays many important roles including air-entrainment control and WIT(Wound In Tension) regulation. The behavior of contact roll significantly affects the winding tension characteristics specifically at the time of contact when the speeds of contact roll and the winding roll are not synchronized. A mathematical model for the web, the winding roll, and the contact roll is derived. By using the model derived, a nonlinear PID(NPID) controller is designed to control the winding tension at the time of contact and separation between the contact roll and the winding roll. Computer simulation study showed that the performance of the winding system with the NPID controller significantly improved compared with that of a system with PID controller.