The aim of the research on which this article is based was to understand the behavioural changes of the target student population over time to ensure that future prevention programmes are more effective in changing behaviour. This study reports on quantitative data collected at the University of the Western Cape over a six-year period between 2007 and 2012. All the students attending the orientation sessions and who were willing to complete the anonymous questionnaire during each of the six years were included in the study. Data were collected on the following aspects and subjects: sexual activity, age at first sexual encounter, number of sexual partners, condom usage, knowledge of how to use a condom, perceived ability to discuss condoms usage with a sexual partner, perception of HIV risk and HIV testing as well as the intention to be tested. Reported alcohol and drug usage, as well as depressive symptoms, was also recorded. The percentage of students reporting having had vaginal sex prior to entering university increased from 44% in 2007 to 51% in 2012 but, alarmingly, the consistent use of condoms decreased from 60% in 2007 to 51% in 2012. The average onset age of about 15.6 years for males and 16.7 years for females for vaginal sex did not change over the six-year period. No difference in smoking patterns or drug use was seen over the period of the study, but the number of entering students who indicated that they consumed alcohol increased significantly from 48% in 2007 to 58% in 2012. HIV testing increased from 19% in 2007 to 47% in 2012, whereas the intention to be tested showed no significant change over the period. Although students increasingly reported that they knew enough about HIV/AIDS (63% in 2007 and 69% in 2012), about a third reported suffering from AIDS fatigue. Prevention efforts targeted at those incoming first-year students who are not yet sexually active (about 45% in this study) should be developed and should take into account the multiplicity of factors that appear to influence their sexual debut.