Winding is used as a final process in roll-to-roll manufacturing system. A wound product can be volume-efficiently stored using this technique, however, excessively large radial direction stress could cause defect in wound product. Maximum radial stress is major cause of material defect, and this has been actively researched. Traditional models of radial stress were focused on uncoated substrate. However, in recent studies based on roll-to-roll, there are many cases of multi-layer coating films having a structure of more than one layer. Therefore, it is also necessary to perform an analysis reflecting the geometry of the coating film on the flexible substrate. In this study, radial stress prediction of the coating material was performed by finite element analysis.