The painful, extremely expressive wooden crucifixes attributed to the Split canon and woodcarver Juraj Petrović occupy an important place among the woodcarving works of 15thcentury Dalmatia. Information about the life and woodcarving activity of this enigmatic personality is contained in only a modest number of archival documents created between 1441 and 1486, in which he is mentioned as a canon and primicerius of the Split cathedral, but also as a woodcarver. In addition to two signed crucifixes, one in the Šibenik Cathedral and another in the church of Our Lady of the Angels in Orebić, other works attributed to Petrović through stylistic analysis include the crucifixes in the church of St. Blaise in Pridvorje, in Split Cathedral of the Assumption of the Blessed Virgin Mary (or Saint Domnius), in the parish church of St. Michael in Omiš, in the Hvar Cathedral of St. Stephen as well as the statues of the Virgin and St. John from the Crucifixion group made for the church of St. Frane in Šibenik. There are several other crucifixes that display similar stylistic tendencies, but whose authorship is ultimately uncertain. Namely, they include the crucifixes in the church of St. Francis in Šibenik, in the Holy Cross church on Čiovo, in the Holy Cross church in Gruž and in the church of the Franciscan monastery of the Exaltation of the Holy Cross on Krapanj. By using naturalistic elements to emphasize the torture and pain the Saviour endured, such as those that appear on the numerous crocefissi dolorosi of the 14th century, and by reconciling them with the new, harmonious vision of the human body brought on by the Renaissance, Petrović developed a recognizable and distinctive style that sets him apart as one of the most important sculptors of 15th century Dalmatia. This paper contextualizes the emergence of the phenomenon of "painful crucifixes", it provides an overview of archival documents in which the name of the master Juraj Petrović is mentioned, analyzes his signed works and those attributed to him with greater or lesser certainty, and it also refers to existing issues related to the attribution of certain crucifixes.