Bernard’s ‘Sermones super Cantica Canticorum’ is his masterpiece and the superlative achievement of his mystical theology. The aim of this paper is to explore Bernard’s sermons introductorily, i. e. their background, literary form, contents, to put them across in their entirety. The Canticle is interpreted allegorical as follows: christological (ecclesiastical), mystical, mariological. In accordance with the traditional interpretation, Bernard interprets the bride as the soul thirsting for God. In addition, he links the traditional allegorical interpretation with the individual experience which the religious subject has. Although Bernard preached to his community, it seems, on the basis of evidence from the letters and the sermons, that Bernard’s 86 sermons on the Song of Songs are so much edited and altered, and they do not exhibit us the sermons as preached. So they are to regard as ‘more the product of the scriptorium rather than the pulpit’, more the literary work rather than the oral sermon. The mystical theology, which is contained in the sermons, is first the nuptial (bridal) mysticism. The bride is the individual soul loving God, and her ultimate aim is the mystical union with God (spiritual marriage). Bernard depicts this religious development with three kind of kisses. Second, his mystical theology is the Christ-mysticism. Bernard concentrates his meditative, contemplative attention on the suffered, crucified Christ. Therefore, his mysticism is to call as suffering-mysticism (cross-mysticism). The character of his mysticism is the emphasis on the experience. The spiritual experience is for Bernard the source of the religious, theological knowledge. The central experience is both self-knowledge and God-knowledge, and both are inevitable for our salvation. Finally, Bernard’s mysticism has the traditional structure of the mysticism, yet it also is to designate as the latin mysticism which is christ-centric and emphasizes the love and the experience. Bernard’s mystical sermons on the song of songs do not aim at knowing the divine mysteries but consummating spiritual union with God.