Background: High-risk pregnancies contribute substantially to maternal and perinatal morbidity and mortality, especially in low-resource settings. Early identification of risk factors and timely obstetric intervention are essential to improving outcomes. This study evaluated perinatal outcomes associated with various high-risk conditions among women attending a tertiary rural healthcare centre. Methods: A cross-sectional observational study was conducted over 2 years (November 2020–November 2022). A total of 310 high-risk pregnant women were enrolled. Detailed antenatal history, clinical examination, laboratory investigations, and ultrasonography findings were recorded. Perinatal outcomes—including mode of delivery, birth status, birth weight, congenital anomalies, NICU admission, need for surfactant or ventilatory support, and mortality—were documented. Data were analysed using SPSS v21, and associations were tested using the Chi-square test, with p < 0.05 considered significant. Results: The most prevalent high-risk factors were anaemia (8.71%), gestational hypertension (8.06%), pre-eclampsia (9.68%), IUGR (5.80%), and oligohydramnios (6.45%). Caesarean section was the commonest mode of delivery (60%). Of 322 neonates, 294 (91.4%) were live births, 23 (7.14%) were stillbirths, and 5 (1.55%) were neonatal deaths. Abruptio placenta showed a statistically significant association with stillbirth (p = 0.008). Preterm delivery and eclampsia were significantly associated with surfactant requirement, while preterm birth, instrumental delivery, and oligohydramnios were significantly associated with pathological jaundice. No significant association was found between congenital anomalies and maternal risk factors. Conclusion: Hypertensive disorders, anaemia, placental complications, prematurity, and oligohydramnios remain major contributors to adverse perinatal outcomes. Abruptio placenta is strongly linked to stillbirth, while prematurity significantly affects neonatal morbidity. Strengthening antenatal surveillance, early risk stratification, and timely referral can substantially reduce preventable perinatal morbidity and mortality in high-risk pregnancies.