It has been suggested that the risk of adverse perinatal outcomes in twin pregnancies is exacerbated by concomitant gestational diabetes mellitus (GDM). This study aimed to assess the risk incurred by twin pregnancy and by a diagnosis of GDM, separately, on the development of poor perinatal outcomes. A retrospective cohort study was conducted on all pregnant women at a tertiary center between 2016 and 2017. The impact of GDM and twin pregnancies on perinatal outcomes — birth weight above the 90th centile for gestational age, cesarean delivery, clinical neonatal hypoglycemia, and premature delivery (before 37 weeks’ gestation) — was assessed using univariate and multivariate analyses. Overall, 13,527 women were eligible for the study; 11,915 were uncomplicated singleton pregnancies; 1379 of these had GDM; 194 were twin pregnancies, and 39 of these had GDM. Univariate analyses showed that twin pregnancies were associated with a higher risk of all perinatal outcomes except macrosomia. In the multivariate analyses, twin pregnancy was a much higher predictor of cesarean delivery (OR 8.40, 95% CI [6.25, 11.49], p < .0001) and preterm birth (OR 58.82, 95% CI [31.25, 125], p < .0001) compared to GDM but GDM was a higher predictor of neonatal hypoglycemia (OR 4.87, 95% CI [3.74, 6.29], p < .0001). Twin pregnancy is more strongly associated with all adverse perinatal outcomes except macrosomia. GDM does not increase risk of adverse perinatal outcomes except for neonatal hypoglycemia.