The increased potential for negative pregnancy outcomes in both extremes of reproductive age is a well-debated argument. The aim of this study was to analyze the prevalence and the outcome of pregnancies conceived at extreme maternal ages. This retrospective study considered all single consecutive pregnancies delivered in a tertiary referral center between 2001 and 2014. Patients were categorized into 4 groups according to maternal age at delivery (< 17 years; 18–28 years; 29–39 years; > 40 years). The following outcomes were considered (amongst others): pregnancy-related hypertensive disorders (PRHDs), neonatal resuscitation (NR), neonatal intensive care unit (NICU) admission, periventricular leucomalacia (PVL), and grade 3 and 4 intraventicular hemorrhage (IVH). During the considered period 22,933 single pregnancies gave birth in our unit. We observed 71 women aged < 17 years, and 1552 aged > 40 years. In each year throughout the study period, there was a significant increment in maternal age of 0.041 years (95% CI 0.024–0.058) every new year. Multivariate analysis concluded out that maternal age over 40 years was an independent risk factor for preterm delivery (OR 1.36 95% CI 1.16–1.61, p < 0.05, PRHDs (OR 2.36 95% CI 1.86–3.00, p < 0.05), GDM (OR 1.71 95% CI 1.37–2.12, p < 0.05) cesarean section (OR 1.99 95% CI 1.78–2.23, p < 0.05), abnormal fetal presentation (OR 1.29 95% CI 1.03–1.61, p < 0.05), and fetal PVL (OR 3.32 95% CI 1.17–9.44, p < 0.05). We also observed that maternal age under 17 years or over 40 years was an independent risk factor for grade 3 or 4 neonatal IVH (OR 2.97 95% CI 1.24–7.14, p < 0.05). These findings confirm a negative impact of extreme maternal ages on pregnancy. These results should be carefully taken into account by maternal care providers in order to inform women adequately, supporting them in understanding potential risks associated with their procreation choices, and to improve clinical surveillance.