The aim of this work was to develop a tablet for the buccal delivery of the poorly soluble drug carvedilol (CAR), based on poly(ethyleneoxide) (PEO) as bioadhesive sustained-release platform and hydroxypropyl-β-cyclodextrin (HPβCD) as modulator of drug release. As first, PEO tablets loaded with CAR/HPβCD binary systems with different dissolution properties were tested for CAR and HPβCD release features and compared to PEO tablets containing only CAR. When the drug was incorporated as CAR/HPβCD freeze-dried product, all CAR content was released from the tablet in about 10 h, displaying a constant release regimen after a transient. The effect of HPβCD incorporation on the release mechanism, was rationalized on the basis of the interplay of different physical phenomena: erosion and swelling of the tablet, drug dissolution, drug counter-diffusion and complex formation. In the second part of the study, the potential of HPβCD-containing PEO tablets as buccal delivery system for CAR was tested. It was found that the incorporation of HPβCD in the tablet did not alter significantly its good adhesion properties. The feasibility of buccal administration of CAR was assessed by permeation experiments on pig excised mucosa. The amount of CAR permeated from PEO tablet was higher in the case of HPβCD-containing tablets, the maximum value being obtained for CAR/HPβCD freeze-dried system. Our results demonstrate that, when the tablet is employed as transmucosal system, the role of drug dissolution enhancement in the hydrated tablet is much more relevant than in solution for increasing the delivery rate.