Abstract Background Hypertensive disorders during pregnancy continue to increase in prevalence and are associated with several adverse outcomes and future cardiovascular risk for mothers. This study evaluated the association of hypertensive disorders compared to no hypertension during pregnancy with neonatal and maternal outcomes. We then evaluated risk factors associated with progression from a less to more severe hypertensive disorder during pregnancy. Methods We conducted a propensity-matched retrospective cohort study utilizing Medicaid claims data from a national insurer. The study population consisted of mothers with and without hypertensive disorders who delivered between 7/1/2016–12/31/2018 and their infants. Hypertensive disorders included gestational hypertension, chronic hypertension, preeclampsia, and superimposed preeclampsia. Propensity score matching was used to match mothers without to those with hypertensive disorders. Regression models were used to compare maternal and neonatal outcomes. Stepwise logistic regression was used to determine characteristics associated with the progression of gestational hypertension to preeclampsia or chronic hypertension to superimposed preeclampsia. Results We observed the highest risk of cesarean delivery (odds ratio [OR]:1.61 and 1.99) in mothers and preterm delivery (OR:2.22 and 5.37), respiratory distress syndrome (OR:2.39 and 4.19), and low birthweight (OR:3.64 and 9.61) in babies born to mothers with preeclampsia or superimposed preeclampsia compared to no hypertension, respectively (p