The 16th century was a century during which Habsburgs and the Ottomans had confronted to preserve existing areas of influence and to take possession of new ones. While on the lands Ottomano-Habsburg wars were concentrated on Hungary; on the seas, after being tied the Spanish Empire to the Habsburg dynasty in the person of Charles V, it took its place in history as the Spanish-Ottoman struggle. In this period, one of the important front lines of struggle between Ottomans and the Spanish in the Mediterranean was Algeria, Tunisia, and the nearby islands. The Ottomans, who gained a foothold in a short time in this region by protecting the skilled pirates and overcoming the logistic difficulties with the French alliance, frequently targeted Spanish lands to consolidate their presence in the region. Especially, the Spanish-dominated Balearic Islands were the target of unabated attacks during this period. Despite of being only one of these attacks, the Ottomans invasion of Ciutadella on the North-West slope of the Island of Menorca was the most serious attack in terms of the destruction it caused and thus its place in the collective memory. The incident in question was an indelible mark on the memory of the defeated people of the island and was a sign indicating an important phase that would lead to the Battle of Djerba in 1560. In the present study, the course of events of the Ottoman attack, which is commemorated even today each year as ‘the year of bad luck’ on the island will be analyzed. For this purpose, the subject will be dealt with, in the light of Spanish and Catalan sources, in its different aspects unknown or ignored in the studies on the Ottoman history in Turkey.