‘Deterrence’ has been a cornerstone for national security of great powers and eventually, the international security during prolonged decades of cold war. However, following the complex changes in the post cold war era, this notion, called ‘complex deterrence’, has undergone massive changes from theory and political strategy aspects. This study is going to present a comprehensive analysis over a part of complex deterrence under the subtitle of ‘Unconventional Asymmetric Deterrence’ which implies unbalanced relationship between two relatively strong and weak actors. The study contends that the adoption of the unconventional deterrence strategy by an expansionist and revisionist would-be nuclear weak-state cannot be considered as reliable national security doctrine and leads deterrence to fail. This conclusion will be achieved upon literature review of the texts and declassified documents derived from US-Iraq confrontations -during the years between two Persian Gulf wars (1991-2003) as well as the post second war insurgency followed by Iraqi regime’s fall.