The extractability of the main oak ellagitannins has been studied in five model solutions containing different types of oak chips (two sizes and different toasting degrees for each size). A new extraction kinetic model has been proposed from the quantitative experimental results obtained by means of HPLC–ESI-MS/MS-multiple reaction monitoring method. The model considers an initial extraction (i.e., washing step) followed by a diffusion step, which involves two different processes that follow first-order kinetics at different rates. Differences in the extractability of the ellagitannins in the different model solutions have been observed and explained on the basis of the kinetic model here proposed.