With the collapse of the Soviet Union, the relative stability that prevailed in the Caucasus region during the Cold War period dissolved into instability and conflicts. This article is based on a comparative analysis of Turkish foreign policy in the context of the Azerbaijan-Armenia conflicts. During the First Nagorno-Karabakh War, Türkiye gave political and military support to Azerbaijan, but this support was not sufficient to change the course of the conflict. Türkiye showed an ardent interest in playing a mediator role. However, its mediator role was limited due to domestic and external circumstances. During the Nakhchivan conflict, Turkish policymakers brought up the possibility of interfering militarily to end the conflict in line with Türkiye’s legal commitments. However, Türkiye’s pro-Azerbaijani position took the form of discursive reactions and border militarization. When the Second Nagorno-Karabakh War erupted in 2020, Türkiye played a much more assertive role to the point of actively contributing to tilting the balance in favor of Azerbaijan. This article compares Türkiye’s position on the Azerbajani-Armenian conflicts and discusses its impacts and implications in the context of the regional dynamics.