Objectives: To compare the perceptions of dental students over a 5-year period. Methods: This cohort study was carried at Taibah University, College of Dentistry, Al-Madinah Al-Munawwarah, Saudi Arabia between 2009 and 2014. Data was obtained using the Dundee Ready Education Environment Measure (DREEM), which consists of 50 items, 4 of these were irrelevant to this cohort and were excluded. All students registered in 2009 were included and followed up in 2014. Their responses were compared using the paired student’s t-test. Results: Thirty-four students completed the questionnaire in 2009, and 30 of them participated in 2014 (12% drop out rate). The mean domain and total scores decreased over time. The mean scores for 6 items decreased significantly, while 4 of them had a significant increase. The lowest mean score in 2009 regarding support for stressed students increased (p=0.004) in 2014. However, the highest mean score in 2009 related to having a good social life, reduced (p=0.007) in 2014. This could be an indication of the high workload and its impact on their social lives. Conclusion: Student’s perceptions were relatively low at the beginning, and remained low throughout the study. There were no significant changes in mean domain, and total scores and although scores of some items improved, most decreased over the study period.