Homiletical scholarship is divided on how Christology should impact Old Testament exposition. Christocentric homileticians argue that every OT text should be connected in some way with God's revelation and redemption in Christ. On the other hand, Christiconic homileticians argue that Christ as the fulfillment of true humanity provides a warrant to show how each OT text calls us to obey God's will. This thesis seeks demonstrate that both approaches are undergirded by the same theological substructure and are thus complementary rather than contradictory. To investigate this claim, the study undertakes an exegetical study of two Pauline texts -- 2 Cor 6:14-18 and 1 Cor 10:1-22 -- with a view to answering the following question: What is it about Paul's understanding of redemptive-history that allows him to use the OT as a source of moral exhortation? In each of these texts, Paul reads the OT as both a foreshadowing of Christ and a source of instruction for the Christian life. After studying these two NT texts, the thesis surveys three motifs in biblical theology that shed light on the broad theological context for Paul's homiletical exhortation -- new creation, new covenant, and new exodus. Each of these motifs plays a role in 2 Cor 6:14-18 and 1 Cor 10:1-22, and they shed further light on why a Christocentric hermeneutic is inseparable from the hortatory function of Scripture. A survey of theological anthropology follows and puts our exegetical findings in conversation with systematic theology. Here it is suggested that understanding Christ as the fulfillment of true humanity is a theological reality that undergirds the dual function of typology as something that is both anticipatory and hortatory. Yet this raises a homiletical question: Does the Christ-centeredness of the canon as a whole necessitate that every individual OT sermon be Christocentric? To address this question, we explore the general and special hermeneutics of canonical plot structure, offering two resources -- the medieval fourfold method of interpretation and a theodramatic model of doctrine -- for a homiletic that can operate at multiple levels of canonical specificity. Finally, we draw these theoretical conclusions together in order to propose a constructive model for understanding the move from text to sermon. This model is built on our exegetical findings and informed by our discussions of theological anthropology and canonical plot structure. We propose that Paul utilizes the OT for Christian instruction by drawing canonical correspondences of response between God0́9s people at various points in redemptive history. Finally, we offer some hermeneutical and pastoral guidelines for drawing such correspondences in preaching. Thus the thesis is an integrative study that seeks to wed homiletical theory with pastoral practice.