A winding model for prediction of in-roll stress distribution, considering air leaking effect is presented. Air layer is formed between webs within wound roll due to air entrainment, and then the air layer thickness varies with air leakage of the widthwise edges of wound roll while winding. It alters the stress distribution with reducing apparent roll stiffness. In this study, on estimating the air layer thickness, the air flow between webs is assumed as an incompressible squeeze flow between parallel plates in web-width direction. Additionally, it is extended to take into account that the stress at the already-wound part of the roll is sequentially varied from continuous web winding. Experimental validation result states that predicted value corresponds well to the experimental value. Furthermore, influence of air leaking effect on n-roll stress is verified by a parametric study.