HIV infection and adolescent pregnancy are known to increase the risk of adverse perinatal outcomes. However, data are limited concerning the outcomes of pregnancies among adolescent girls living with HIV. This retrospective propensity-score matched study aimed to compare adverse perinatal outcomes in adolescent pregnant women living with HIV (APW-HIV-positive) with HIV-negative adolescent pregnant women (APW-HIV-negative) and adult pregnant women with HIV (PW-HIV). APW-HIV-positive were propensity-score matched with APW-HIV-negative and PW-HIV. The primary endpoint was a composite endpoint of adverse perinatal outcomes, comprising preterm birth and low birth weight. There were 15 APW-HIV-positive and 45 women in each control group. The APW-HIV-positive were aged 16 (13–17) years and had had HIV for 15.5 (4–17) years, with 86.7% having perinatally acquired HIV. The APW-HIV-positive had higher rates of perinatally acquired HIV infection (86.7 vs. 24.4%, p < 0.001), a longer HIV infection time (p = 0.021), and longer exposure to antiretroviral therapy (p = 0.034) compared with the PW-HIV controls. The APW-HIV-positive had an almost five-fold increased risk of adverse perinatal outcomes compared with healthy controls (42.9% vs. 13.3%, p = 0.026; OR 4.9, 95% CI 1.2–19.1). The APW-HIV-positive and APW-HIV-negative groups had similar perinatal outcomes.