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Given that different generations of gay, bisexual, and other men who have sex with men (gbMSM) have been influenced by substantially different life course events and cultural contexts, we explored differences in sexual behaviour between millennials, Gen-Xers, and baby boomers. Sexually active gbMSM from Metro Vancouver, ≥ 16 years, were recruited using respondent-driven sampling between 2012–2015 and completed computer-assisted self-interviews every 6 months, up to 2017. To explore differences between generations (millennials born ≥ 1987, Gen-Xers born 1962–1986, baby boomers born < 1962) we used multivariable logistic regression models using baseline, RDS-weighted data. We also examined 6-month trends, stratified by generation, in partner number, prevalence of high-risk sex, and relationship status using hierarchical mixed-effects models. Among 774 gbMSM (190 millennials, 469 Gen-Xers, 115 baby boomers), median age of first anal sex with a male partner decreased from 20 (aQ1,aQ3:17,25) among baby boomers to 18 (aQ1,aQ3: 16,20) among millennials (x2 (DF = 2, N = 764) = 12.920, p = 0.002). After controlling for relevant demographics, differences were observed for some sexual behaviours (i.e., anal sex positioning, giving oral sex, sex toys, masturbation, sexual app/website use, transactional sex) but not others (i.e., receiving oral sex, rimming, fisting, watersports, group sex). At baseline, millennials reported less high-risk sex than other generations but all trended toward less high-risk sex, fewer partners, and regular partnering over the course of the study. While there was notable similarity across generations, millennial gbMSM reported earlier age at first anal intercourse and less high-risk sex. However, all generations trended towards less high-risk sex, fewer partners, and regular partnering over time.