Background/Objectives: Women with polycystic ovarian syndrome (PCOS) are at higher risk for pregnancy complications. The PCOS population is heterogeneous, with different phenotypes linked to varying risks of adverse outcomes. However, literature on pre-conceptional hyperandrogenism is limited and based on small sample sizes. Methods: This multi-institutional retrospective cohort study included pregnant patients diagnosed with PCOS with or without pre-conceptional hyperandrogenism. Utilizing the TriNetX platform, one-to-one propensity score matching was conducted to adjust for factors such as age at pregnancy, race, chronic diseases (e.g., diabetes and hypertension), and body mass index. Exclusion criteria included multiple pregnancies and patients who received assisted reproductive technology, oral contraceptives, or spironolactone. 571 patients with PCOS and pre-conceptional hyperandrogenism and 13,465 patients with PCOS without hyperandrogenism were identified. Post-propensity matching, each cohort consisted of 564 patients. Results: Pregnant women diagnosed with PCOS and pre-conceptional hyperandrogenism showed a higher risk of adverse maternal and neonatal outcomes compared to those diagnosed with PCOS but without hyperandrogenism. There was a higher incidence of large for gestational age (6.6% vs. 3.9%, OR = 1.73, 95% CI [1.007-2.972], p-value = 0.045) and preterm birth (10.3% vs. 5.9%, OR = 1.844, 95% CI [1.183-2.876], p-value = 0.006), but had no significant increase in the risk of gestational hypertension, preeclampsia/eclampsia, gestational diabetes, missed abortion, intrauterine growth restriction, placenta abruption, or cesarean section. Conclusions: Women with PCOS and pre-conceptional hyperandrogenism face a greater risk of pregnancy complications. Further studies are needed to clarify the results and mechanisms and determine whether treatment improves outcomes.