Postterm Pregnancy is one of the commonest obstetric conditions which associated with an increased risk of fetal and neonatal mortality and morbidity as well as an increased maternal morbidity. The aim of the present study is to determine the maternal and fetal outcomes of postterm pregnancy at Al-Sadaqa Teaching Hospital. A prospective case–control study was conducted at Al-Sadaqa Teaching Hospital, Aden from January 1st to December 31th 2020. Cases were considered postterm pregnancy (≥ 42 weeks) while control term pregnancy (37weeks - 41weeksand 6 days). Significant association between gestational age and the studied variables of postterm and term pregnancy were analyzed using appropriate statistical methods. A total of 185 cases of postterm pregnancy and 370 control group of term birth, the frequency of postterm pregnancy was (2.78%), we found statistically significant association between some of socio-demographic factors and postterm pregnancy, cesarean section was higher in postterm group (OR 2.80) with the indications were cephalopelvic disproportion (OR 12.38). Maternal complications were significantly association to postterm birth like prolonged labor (OR 12.99) and postpartum hemorrhage (OR 8.32). Regarding to fetal outcomes, Postterm pregnancy has showed a significant association with neonatal low Apgar score(p=0.000), Oligohydramnios (OR 42.24) asphyxia (OR 2.86), meconium aspiration (OR 9.41) and Perinatal death (p value 0.012). This study concluded that postterm pregnancy is associated with adverse maternal outcomes such as, prolonged labor and postpartum hemorrhage, and associated with adverse fetal outcomes like oligohydramnios, asphyxia and meconium aspiration syndrome. The outcome of prolonged pregnancy can be improved by proper counselling for follow up during pregnancy and proper monitoring and appropriate management during labor.