The author considers the important problem of the Medieval culture relating to the interrelation between human freedom and divine predestination. This theoretical issue is presented throughout the history of Christianity but it was revealed and most actively discussed at the period of Patristics when the Western and the Eastern Church Fathers were elaborating the Christian creed. This paper focuses on the philosophical and theological doctrine of Augustine of Hippo about human's freedom and God's predestination stressing that thereafter the Augustinian viewpoint has been determining the evaluation of Western Christianity. At the same time, it also analyzes Augustine's point of view representing Western Patristics with the corresponding teaching of Eastern Patristics. Special attention is paid to the difference in understanding the role and importance of man in the relationship between personal freedom and the divine predestination.