This paper presents a method of predicting the internal stress states in rolls simultaneously wound with independent supply spools of dissimilar material. The method is based on linear, orthotropic behavior of the mandrel and web materials, and is sufficiently general to allow an arbitrary choice for web materials and their respective winding tensions. The generality of the method also permits the introduction and termination of additional webs of arbitrary material at any time during the winding process. The method is analytical, and utilizes an elasticity solution with rigorous satisfaction of boundary conditions between each ply of the wound roll. A prototypical wound capacitor is used as an example to provide for numerical results of the internal stress states induced during the winding process. Differences in the winding tension loss of the two dissimilar web materials is discussed and explained, as are other mechanical threats to roll stability and performance. The influence of winding tension variations on internal, wound stress states is also discussed