This thesis aims at investigating the use of the Old Testament in the New, and in Hebrews specifically, focusing on two aspects which appear to have been somewhat neglected in previous scholarship, namely the text and context of specific quotations. The aspect of text takes the complicated textual history of the Old Testament into account, especially concentrating on the findings of recent Septuagint research and particularly the possibility that different Hebrew texts may underlie the Greek translation. The aspect of context draws on the assumption that Hebrews was composed in a Jewish context, where the Old Testament text had been interpreted for a long time. It is also presupposed that this exegesis was handed down along with the Hebrew Scriptures not only in the post Second Temple Jewish community, but also in the early Church. Hence primary sources, such as Talmud, Midrash and early Church Fathers, are consulted with the intention of better understanding the interpretation of the Old Testament quotations in Hebrews. To do this three Old Testament texts, which exist in distinctly different versions and have been quoted in Hebrews, have been examined, namely Gen. 47:31b (in Heb. 11:21), Ps. 40:7b (in Heb. 10:5), and Jer. 31:33 (in Heb. 8:10 and 10:16). The outcome of this study shows that several versions of Old Testament texts were interpreted at the time of the New Testament and that the peculiarities of the different versions had a decisive impact on the exegesis of the texts. Further, it shows that some versions of the texts were favoured in the Jewish context while others were preferred in the early Church. Hence different understandings of Old Testament passages in different contexts are sometimes not the result of different interpretations of the same texts, but of the exegesis of different versions of the same text.