The main objective of this work was to apply contact angle analysis to predict work of adhesion (Wa) between some modified wood materials and certain thermoplastics and adhesives. Wetting properties, i.e., contact angles, were measured by the Wilhelmy method on both freshly prepared and aged veneer samples of unmodified and acetylated Scots pine, furfurylated radiata pine, and heat treated Norway spruce. The sessile drop method was used to measure contact angles on a phenol resorcinol formaldehyde, an emulsion polymer isocyanate, and a one-component polyurethane adhesive. Contact angle data were also collected from the literature on polyethylene, polyvinyl chloride, polymethyl methacrylate, polystyrene, and Nylon 6. Contact angle analysis based on the Chang-Qin-Chen model was then applied to determine so-called acid-base interaction parameters and Wa between the wood samples and the selected thermoplastics and adhesives. Results show that the ageing process led to an increased hydrophobic character of unmodified, heat treated, and furfurylated wood samples. The freshly prepared acetylated wood samples had a pronounced hydrophobic character which remained approximately constant after ageing. The predicted Wa between the wood and the adhesives was considerably higher than that between the wood and the thermoplastics. Furthermore, the predicted Wa between the acetylated wood and both the thermoplastics and water was approximately unchanged when comparing the fresh and aged samples. In contrast, the ageing of all other wood samples resulted in a dramatic decrease of the wood-water Wa and a moderate decrease of the wood-thermoplastics Wa. The wood-adhesives Wa, however, was unchanged for the unmodified and furfurylated wood when comparing the fresh and aged samples and even increased for heat treated and acetylated wood samples.