While little research has been conducted into the reproductive experiences of transgender people, available evidence suggests that like cisgender people, most transgender people endorse a desire for these experiences. This study explores the pregnancy experiences and related health factors among transgender and gender diverse 14 to 25 year olds using a national Canadian sample (N = 923). Results indicated that 26 (5%) transgender youth reported a pregnancy experience in the past and the prevalence among 14- to 18-year-olds was comparable to population-based estimates using the same question in the British Columbia Adolescent Health Survey. Transgender youth with a history of pregnancy involvement reported a diverse range of gender identities, and this group did not differ from the remainder of the sample on general mental health, social supports, and living in felt gender. This group did report over six times greater likelihood of having been diagnosed with a sexually transmitted infection by a doctor (19%), but they did not differ in reported contraception use during last sexual intercourse. These findings suggest that pregnancy involvement is an issue that should not be overlooked by health professionals working with transgender youth and that this group has particular sexual health needs.