Through sketches, designers can seek and create more desirable and sustainable forms by transforming previous images through various techniques like visual additions, deletion, and modifications. Transformative skills in the form of freehand sketches appear to induce creative, explorative, open-ended environments that are conductive in dealing with the ill-structured nature of design activities. This study compares sketching and design transformative skills (DTS) between 3rd and 5th year architectural students as measured throughout the discernible levels of diagrammatic, preliminary, refinement, and detail designing. Fourteen architecture students from the University Technology Malaysia (UTM) were observed, with seven respondents each from the third and fifth year student cohorts. The objective of the observation was to capture and analyze the students’ sketches as they design a gallery within the stipulated two-hour period. The research instrument included a set including an HD video camera, drawing instruments, and a brief outline of the design tasks. The Mann-Whitney test was used to determine if there were differences in design transformation activities between third and fifth year students throughout the period of observation. The results reveal significant differences in vertical move transformation between third and fifth year students within the preliminary, refinement, and detail phases of designing.