The liberation of Azerbaijan’s Armenian-occupied territories as a result of 44 days of war laid bare a rarely-discussed topic – the damage caused to Azerbaijan due to Armenia’s illegal activities in the formerly occupied territories. Therefore, this paper seeks to touch upon some of these activities; however, its primary focus is on ascertaining the level of damage caused during the entire period of the Armenian occupation. By highlighting the financial parameters and legal ramifications of the illegitimate actions, the article finds that an underlying political motive was cementing the Armenian occupation and promoting annexationism. In fact, the new reality being created on the ground was being used at the diplomatic table by the Armenian government to drive the negotiating process down a blind alley. Meanwhile, an economic aspiration encapsulated gaining financially through the cultivation of agricultural land, use of water resources for electricity production, export of mineral and natural resources, and even drug trafficking. The paper reveals that a military purpose was also pursued latterly with the recruitment of mercenaries and foreign fighters by Armenia. The article concludes that identification of the amount of direct and collateral damage is likely to provide the beginning of a strong legal basis for demanding compensation.