Cybersecurity assessments are critical for ensuring that security measures in organizational infrastructures, systems, and applications meet necessary requirements. Given the significant HTTPS vulnerabilities exposed in recent years, assessing HTTPS deployments is increasingly important. However, there has been no systematic literature review (SLR) comparing different cybersecurity assessment methods specifically for HTTPS deployment security issues. This study aims to address this gap by identifying, analyzing, and comparing various HTTPS deployment assessment methods documented in scientific literature. Our approach involved a structured research methodology with specific inclusion and exclusion criteria for selecting relevant methods. The review utilizes 16 comparison metrics, divided into two categories: critical security metrics, focusing on assessment metrics adopted and the number of vulnerabilities evaluated by each method, and additional metrics assessing the methods’ applicability and effectiveness in real-world scenarios. The findings indicate varied adoption rates of these metrics among the reviewed cybersecurity assessment methods, highlighting the absence of a standardized approach using common, well-defined security metrics for HTTPS deployment assessment. In contrast, merging all the comparison metrics outlined in this review would enable a more in-depth assessment of HTTPS deployment security issues, enhance the quality of reported results, and lead to the development of a more practical assessment method.