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Wooden panel paintings are among the most important historical and artistic artworks from the Middle Ages and the Renaissance period. Currently, they represent a challenge for conservators and scientists who face complex issues related to their conservation. Panel paintings can be considered multilayer objects, that for brevity can be considered to consist of a wooden support and various paint layers. The wooden support is known to be hygroscopic and is continuously seeking hygroscopic equilibrium with the humidity of the environment, thus it tends to deform. Based on various hygroscopic tests carried out on 6 real panel paintings chosen by expert restorers to represent different periods and construction techniques, this paper describes the deformation tendencies of the selected panel paintings. Among possible variables, three most important variables were identified: (a) tree ring orientation of the wooden support, (b) stiffness and (c) emissivity of the paint layers. The internal equilibrium of the forces, governed by the moisture gradients across the thickness of the wood, changes drastically according to the varying characterisation of these factors. To observe their individual contributions, the 6 panel paintings underwent various humidity cycles, were completely free to deform and were always in complete safety. To characterise the stiffness and emissivity of the paint layers, the 6 panel paintings underwent a few humidity cycles with the front face totally waterproofed; thus, the moisture exchange was forced from the back only, and one of the three variables was eliminated. A complex system emerges where the tree ring orientation of the wooden support, the stiffness and emissivity of the paint layers are strongly coupled and determine the deformation modes of the panel paintings. A numerical analysis was conducted to classify the various general deformation modes of panel paintings and the specific classification of the 6 real panel paintings analysed experimentally. The complexity of the interaction of the variables studied suggests that experimental procedures must be conducted in preparation for numerical analyses of real panel paintings.