The fifteenth century represents a period of affirmation in the expansionist strategies of Portugal and Castile. The study of the military actions of these two Iberian kingdoms can benefit from an integrated, transnational analysis, allowing for the perception of comparisons and political and military interrelations that occurred during this period. This article seeks to analyze and compare the guerrilla warfare conducted by Portugal and Castile against their neighbouring Muslim kingdoms through Portuguese, Castilian, and Muslim chronicles. In the Portuguese case, the analysis focuses on the operations that, from Ceuta and Alcácer-Ceguer, ravaged the Rif region in the Kingdom of Fez between 1415 and 1464. For Castille, special attention is given to the raids carried out during the conquest of the Kingdom of Granada, from 1481 to 1492. The study demonstrates the decisive role of raids and their interconnection with siege warfare and the political control of the territories.
