The heterogeneous data acquired by educational institutes about students’ careers (e.g., performance scores, course preferences, attendance record, demographics, etc.) has been a source of investigation for Educational Data Mining (EDM) researchers for over two decades. EDM researchers have primarily focused on course-specific data analyses of students’ performances, and rare attempts are made at the domain level that may benefit the educational institutes at large to gauge and improve their institutional effectiveness. Our work aims to fill this gap by examining students’ transcripts data for identifying similar groups of students and patterns that might associate with these different cohorts of students based on: (a) difficulty level of a course category, (b) formation of course trajectories, and, (c) transitioning of students between different performance groups. We have exploited descriptive data mining and visualization methods to analyze transcript data of 1398 undergraduate Computer Science students of a private university in Pakistan. The dataset includes students’ transcript data of 124 courses from nine distinct course categories. In the end, we have discussed our findings in detail, challenges, and, future work directions.