Background: Adolescent pregnancy represents an important public-health problem due to its maternal and fetal outcomes. Adolescent patients are predisposed to multiple obstetrical complications, including anemia and preterm birth which has a higher incidence among this population; withal, in the specialty literature, anemia is considered to be a risk factor for preterm delivery; furthermore, multiple studies have demonstrated that a very young age is an independent risk factor for preterm birth. Objectives: The study aims to reveal if anemia during adolescent pregnancy has a negative impact on the time and mode of delivery and newborns’ outcomes. Patients and methods: We performed a retrospective multicentric study on adolescent pregnancy. We analyzed 172 patients aged between 13 and 16 years who delivered in two large tertiary hospitals between 1 October 2018 and 15 April 2022. We divided the patients into two groups—a study group (n = 64) with anemia and a control group (n = 108) without anemia. We evaluated the modes of delivery, the times of birth, and the neonatal outcomes by 1-min newborn’s Apgar score, neonatal intensive-care unit (NICU) admission, and the newborns’ weights. Results: The rate of cesarean section was higher in patients with anemia than in the control group (45.31% vs. 38.88%, p < 0.001). We found that patients between 13 and 16 years diagnosed with anemia have a higher risk of preterm birth than those without anemia (35.93% vs. 21.29%, p < 0.001); however, an increased rate of LBW neonates was observed in the anemic adolescent group ≤14 years (p < 0.001). Regarding the newborns’ 1-min Apgar score, NICU admission, no statistically significant differences were recorded between the two groups according to the severity of anemia. In the anemic patients’ group, prenatal screening was identified in 9.37% of cases, while in the control group, in 16.67% (p = 0.034), which represents negative predictive factors, along with a low socio-economic status for the presence of anemia in young adolescent patients. Conclusions: Anemia is a risk factor for preterm birth, LBW, and cesarean section in young adolescent pregnancy. The association of lack of prenatal care and low socio-economic status worsens maternal and neonatal outcomes.