The diptych icon from Kotor (Imago pietatis and the Virgin with the Christ Child), painted probably in 1468, is examined from the aspect of the penitent and ascetic practice of the Kotor flagellants, who commissioned it for their needs. The members of the brotherhood of the Holy Cross particularly revered the cult of the Five Wounds of Christ, the particles of the lignum crucis and the experience of Christ's Passion. The said religious themes are analysed based on the archive material and preserved paintings, connected with this monastic brotherhood of Kotor.