Recent advances in biotechnology have ensured that one of the main olive tree by-products is olive leaf extract (OLE), a rich source in bioactive compounds. The aim of this work was to study the phenolic composition in different OLEs of three Tunisian varieties, namely, ‘Sayali’, ‘Tkobri’, and ‘Neb Jmel’. The in vitro biodigestibility effect after ‘Sayali’ OLE addition to Californian-style ‘Hojiblanca’ table olives was also studied. This OLE contained bioactive molecules such as hydroxytyrosol, tyrosol, oleropeine, Procianidine B1 (PB1), and p-cumaric acid. These compounds were also found in fresh olives after OLE was added. Furthermore, from fresh extract to oral digestion, the detected amount of bioavailable phenol was higher; however, its content decreased according to each phase of gastric and intestinal digestion. In the final digestion phase, the number of phenols found was lower than that of fresh olives. In addition, the phenolic content of Californian-style ‘Hojiblanca’ table olives decreased during the in vitro digestion process. The antioxidant activity of this variety decreased by 64% and 88% after gastrointestinal digestion, being the highest antioxidant capacity found in both simulated gastric and intestinal fluid, respectively. The results show us that the ‘Sayali’ variety is rich in phenolic compounds that are bioavailable after digestion, which could be used at an industrial level due to the related health benefits.