Contraceptive knowledge and use at first sex have increased over time among Jamaican adolescents, yet high unintended pregnancy rates persist. More information on risk factors for adolescent pregnancy is needed to inform programs. Structured interviews were conducted with 15-17-year-old females-250 who were currently pregnant and 500 sexually experienced, but never-pregnant, neighborhood-matched controls. Bivariate and multivariate analyses were used to examine associations between adolescent pregnancy and early sexual debut, sexual coercion or violence and sexual risk-taking behaviors. Greater proportions of pregnant youth than of their never-pregnant peers reported having had first sex by age 14 (54% vs. 41%), a first sexual partner who was five or more years older (33% vs. 20%) or multiple partners (63% vs. 50%); a greater proportion of never-pregnant youth had used contraceptives at first sex (88% vs. 80%). Almost half (49%) of all young women reported ever having experienced sexual coercion or violence. Compared with controls, pregnant youth had greater odds of having had an older partner at first sex and believing contraception is a woman's responsibility (odds ratios, 1.3 and 2.1, respectively), and had lower odds of ever having experienced sexual violence and thinking that it is important to protect oneself against pregnancy (0.5 and 0.2, respectively). An interaction between early sexual debut and multiple partners was found. Having had multiple partners was associated with pregnancy only for youth with early sexual debut. Encouraging adolescents to delay sexual debut and reduce their number of sexual partners may help prevent unintended pregnancies. Experiences of sexual coercion and violence were common among both groups, highlighting the need to address gender-based violence at the community level.