The objective of the paper was to compare encounters involving unprotected anal intercourse (UAI) and protected anal intercourse (PAI) among HIV-negative gay men in Sydney. Data were from those completing baseline face-to-face interviews to end June 2003 for the Health in Men open cohort of HIV-negative gay men in Sydney. The 1,148 participants ranged in age from 18 to 75 years (median = 36). Three hundred and fifty-two (30.7%) reported an occasion of UAI with a casual partner in the previous 6 months and 531 (46.3%) reported an occasion of UAI with a regular partner in that same time. The men's most recent sexual contact with a casual partner involving UAI was distinguished from those involving PAI by a greater likelihood for both partners to disclose HIV serostatus (p = 0.006) and by respondents being more inclined to restrict themselves to the insertive position or to practise withdrawal during occasions involving any UAI than when a condom was used (p = 0.003 and p = 0.001 respectively). Neither location nor recreational drug use differentiated men's most recent sexual contacts involving UAI from those involving PAI. The decision by HIV-negative gay men to use condoms during sexual encounters with either regular or casual partners is guided more by HIV serostatus and risk reduction strategies than by other factors.