We can learn lessons applicable to resolving the Northern Territories issue by examining the Åland Island settlement. Based on this idea, this paper addresses the issues relevant to the Ainu, especially the connection between the Åland settlement, the Ainu and the Northern Territories dispute. Involving the Ainu in this way challenges many of the current perspectives on this territorial/border demarcation dispute, but is necessary to help invigorate the stale atmosphere of dominating discourses. In this respect, examining the Åland settlement and international setting of the time will clarify why the Ainu are not included in negotiations today. This paper briefly deals with issues of Åland’s connection to Japan, Ainu and Russo-Japanese Treaties, Japanese colonialism and the League of Nations.