Despite the third party efforts of the significant international and regional organizations, such as the UN and the OSCE, the Upper Karabakh problem remains unresolved for over 20 years. Neither the four resolutions related to Armenia’s invasion of Azerbaijani lands adopted by the UN SC in the early 1990s have worked, nor the formal negotiations over this conflict that have taken place under the auspices of the OSCE Minsk Group for more than 20 years have reached any tangible results. These facts give rise to questions about effectiveness of the role of this institution in reaching a resolution to the conflict. The ceasefire regime is in effect since May 1994 without changing the situation, in which Armenia still keeps about 20 percent of Azerbaijani lands under invasion and is effectively involved in building a new state over the invaded lands. This paper analyzes the effectiveness of UN resolutions in liberating Azerbaijan’s invaded regions, both within and outside of Upper Karabakh, as well as the OSCE mediation efforts to resolve this conflict. It also discusses effectiveness of the negotiation process, and raises a question about impartiality of the mediators and usefulness of the mediation institution of the OSCE in general. It argues that the OSCE Minsk Group has failed to successfully establish and lead the process of negotiations, thus expecting a fruitful yield is not realistic.