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Cyber-attacks have become commonplace in the world of the Internet. The nature of cyber-attacks is gradually changing. Early cyber-attacks were usually conducted by curious personal hackers who used simple techniques to hack homepages and steal personal information. Lately, cyber attackers have started using sophisticated cyber-attack techniques that enable them to retrieve national confidential information beyond the theft of personal information or defacing websites. These sophisticated and advanced cyber-attacks can disrupt the critical infrastructures of a nation. Much research regarding cyber-attacks has been conducted; however, there has been a lack of research related to measuring cyber-attacks from the perspective of offensive cybersecurity. This motivated us to propose a methodology for quantifying cyber-attacks such that they are measurable rather than abstract. For this purpose, we identified each element of offensive cybersecurity used in cyber-attacks. We also investigated the extent to which the detailed techniques identified in the offensive cyber-security framework were used, by analyzing cyber-attacks. Based on these investigations, the complexity and intensity of cyber-attacks can be measured and quantified. We evaluated advanced persistent threats (APT) and fileless cyber-attacks that occurred between 2010 and 2020 based on the methodology we developed. Based on our research methodology, we expect that researchers will be able to measure future cyber-attacks.