Insurgency and its tactics are as old as warfare itself. Most modern warfare occurs in the form of insurgencies which has become a rather problematical term. It is probably fair to say that in many ways it mixes with peaceful calls for self-determination or the public demands for reforms. One of the main objectives of many insurgency movements is to replace the existing government and make an alternative one acceptable to the people. In doing so, insurgents follow different tactics as they engage in guerrilla warfare. There is a great debate about the nature of counter insurgency operations. Is it purely part of the military operations? Or is it rather civilian-centric efforts with the support of security forces? To this day we remain unconvinced regarding the best way of approaching counter insurgencies. As a concept, the "insurgent" term remained elusive too. Some of the literature in this field has been preoccupied with the power values based on the realist theory which provides a powerful basis for explaining the aggressive military behavior against insurgents. In the absence of measurable methods within which we might interpret success or failure, counter insurgency operations remain very complicated to evaluate. The traditional metric of success in conventional warfare focuses on "defeating the enemy" or the use of all possible means to force him to surrender. This metric is inapplicable in the counter insurgency operations where the main purpose is to gain the people's support and persuade the insurgents to join the government side with limited use of force. Being one of the main pillars of the classical British school of counter insurgency, "winning hearts and minds" remain the dominion in all British operations. The purpose of this study is to examine the British approach to counter insurgency in the Sultanate of Oman during twentieth century. The reason is that local literature reveals the absence of a comprehensive study that critically analyses Omani insurgencies and evaluates the extent to which Britain employed the principle of "winning hearts and minds". This study intends to explore how the counter insurgencies were won based on analyses of two case studies namely: Al Jebel AlAkhdar War (1957 - 1959) and Dhofar War (1965 - 1975).