With the continuing advancement in material technology and construction techniques, architects face a greater set of options and challenges when it comes to designing in historic settings. In the meantime after the ICOMOS agreement, every country adapted the policy according to their own culture and settings, therefore every architect in their respective country started interpreting the charters, and the design review processes in their own way. Working on the new addition to historic context gave rise to familiar characteristics in design, especially in the infill designs, which is “Replication and Contrast”, which in turn sparked the question, how to evaluate whether a building is properly fitting in its context with whatever approach employed. This paper aims to answer this question by conducting a literature review covering First, the qualitative evaluation approach which compromises of surveys and pre-visualization in order to identify the main visual properties that improve the contextual compatibility of the new designs in the historical context, and quantitative techniques focused more on the mathematical scientific cognitive results of all aspects of the architectural elements within historic settings. A comparison has been made on each result achieved and an assessment of their reliance or authenticity has been tested in order to find and bridge the gap between tangible and intangible values when judging “fit” in a historic setting. The results showed that the qualitative evaluation if followed properly it could be very promising, but it always leaves room for skepticism as the result is expected to change based on the size and the characteristics of the participants. The quantitative evaluation provided a more tangible evidence of the contextual fit in terms of architectural elements like size, proportion, and scale. Finally, a suggestion was made in order to provide a better, and a more comprehensive technique merging both methods together and trying to incorporate more of three-dimensional aspects of the building instead of the two dimensionality of the current assessment techniques.