It is known that the systematic devastation of the territory and the economic resources of the opponent assumed, during the armed conflicts between municipalities of central northern Italy, a prominent role. In spite of such a finding, however, the historiography available on the subject – obviously with due exceptions – is limited to ascertaining its presence, or to underlining the preponderance of the occurrences over different forms of military practice such as siege and battle, but without formulating appropriate interpretative schemes. The distant suggestions of writings in English, and in particular of the Western Art of the War of Victor Davis Hanson, too distant, however, both in time and space, from the Middle Ages of Italian cities, and therefore paradigms to be considered with prudence, are sometimes dominant. The proposed work retraces the issues mentioned above, proposing a new reading of what has been known so far in the Italian municipal sphere. Starting from the analysis of the systematic devastations, it is therefore attempted to highlight a deep but elusive dynamic of the war practice operating in Italy of the cities: considering the crops destroyed by raids, the way in which they were conducted, the troops thus employed and the concrete and psychological results of such operations, the aim is finally to highlight the close relationship between this practice and the siege operations properly understood.It is well known how the systematic devastation of the territory and the economic resources of the adversary assumed, during the armed conflicts between cities of central northern Italy, a major role. In spite of similar remarks, still, the Historiography available on the subject – obviously with the two exceptions – limits itself to ascertaining the presence, or underlining the Predominance of the occurrence in respect to different forms of military policies of siege and battle, without, however, formulating adequate interpretive schemes. Therefore, it sometimes results dominant, in an uncrowded panorama of studies, the far away written suggestions in English, and in particular the Western Art of the war of Victor Davis Hanson, too distant, though, both in time and space, from the medieval Italian cities, and, hence, paradigms to be prudentially considered. The work proposed travels along the above mentioned subjects, proposing a new reading of that to date is known on the subject within the sphere of Italian cities. Starting from the scrutiny of the systematic devastation it attempts to shed light on profound but elusive dynamics of the wartime policies used in Italy by the cities: considering the cultivation that was destroyed time after time by the raids, the way in which they were conducted, the troops employed and the tangible and psychological results of similar operations, finally, it is proposed to highlight the close relationship existent between such policies and the very intense siege operations.