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A significant contribution to the oeuvre of Niccolo di Giovanni Fiorentino who, according to the sources, was active between 1464 and 1505, is the tombstone of Canon Matej Sturarius in the Church of Our Lady of Olives at Zadar, which Ivo Petricioli attributed to this sculptor. The inscription on the tombstone informs us that the canon, who was a close collaborator of Archbishop Maffeo Vallaresse, commissioned the monument while still alive but unfortunately, given that the year of his death remains unknown, this piece of information does not provide a basis for the dating of the tombstone. Nonetheless, a more detailed analysis of it yields new arguments which support a hypothesis that Niccolo di Giovanni Fiorentino developed his artistic profile in the workshop of mature Donatello. One arrives at this conclusion first and foremost by comparing the Zadar tombstone with those which were made by Donatello, for example the tombstone of Giovanni Crivelli (Rome, S. Maria in Aracoeli) and the tombstone of Pope Martin V (Rome, S. Giovanni in Laterano), while the closest parallel can be found in the tombstone of Bishop Giovanni Pecci (Siena Cathedral) which has been dated in the recent literature to the late 1540s. The tombstone of Bishop Pecci is characterized by a range of visual innovations through which the figure of the deceased and the architectural frame were designed to be seen from below and because of this, it was an important source of inspiration for many Sienese sculptors (such as Urbano da Cortona and Giovanni di Stefano) who borrowed Donatello’s composition or some of its parts for the tombstones they produced during the second half of the fifteenth century. Niccolo’s tombstone at Zadar also displays a reliance on Donatello but not as a direct copy of the constituent parts of the tombstone he made for Bishop Pecci but through the application of similar compositional principles. This is strongly implied by the motif of two crests which can be seen in the upper part of the tombstone. They were depicted in perspective in the manner of Donatello but their decorative role on the tombstone differs from those in the works of Donatello and his followers. The reliance of the Zadar tombstone on that of Bishop Pecci from Siena also opens up a possibility that Niccolo may have spent some time in Siena while Donatello was there (1457–1461) and, judging from the known chronology of his artistic activity, such a connection cannot be excluded. Because the surface of the Zadar tombstone is in a relatively poor state of preservation, the issue of whether it was made by Niccolo himself or with the help of his bottega remains open but, given that the composition is undoubtedly his, this issue remains of secondary importance.