The majority of researchers in air power theory up to this date have studied the use of airpower inconventional wars. This is also the case with the well renowned air power theorist Robert A. Pape.In his academic work Bombing to Win, Pape seeks to find the circumstances for when coercive powersucceeds or fail. After an empirical study, presented in the book, he explains that the extensive useof denial strategies will lead to victory and every other strategy is basically a waste of time. Heclaims that his theory can predict the outcome of 33 air operations during the twentieth century withan accuracy of 93 percent.This study seeks to determine if his claims are true in a non-conventional conflict against an insurgencyor a guerilla. To examine this Pape’s theory is tried against two conflicts in which the oppositionconsisted of irregular forces. Operation Enduring Freedom, when the Americans fought theTaliban and al Qaeda and the South African Border War when the South Africans were in combatagainst a rebellious guerilla.The theory testing case-study shows that Pape’s assumptions to great extent can explain the outcomeof the two conflicts. The denial strategy that Pape advocates where showed to contribute to the greatestmilitary effects.