The prevalence of diseases that complicated childbirth and the postpartum period in the Samara region for the period 2009–2021 was investigated. The study was performed based on the official statistical reporting of the Samara region according to a standard scheme. The structure of pathological conditions was assessed. Then, the dynamics were analyzed, and modeling and medium-term forecasting were conducted. Structure analysis was carried out based on the 2016 data. Forecast was performed for the medium term (5 years). Notably, premature rupture of membranes (55.8%) is the most common complication of childbirth and in the postpartum period, followed by obstructed labor (11.4%), childbirth complicated by umbilical cord pathology (10%), childbirth complicated by hypertensive disorders such as preeclampsia and eclampsia (9.3%), and various labor disorders (9.1%). However, the considered conditions indicated in the official statistical reporting explain only 61.1% of all complications of childbirth and in the postpartum period, and 38.9% of all conditions remain unknown, which makes prevention, timely diagnosis, and effective treatment of these conditions challenging. The underreporting of cases of hypertensive disorders during pregnancy is evidenced by their higher frequency during childbirth. Only 25%–30% are complications during pregnancy of the number of complications of this pathology during childbirth and the postpartum period, and the downward trend in the prevalence of this complication during pregnancy is combined with an upward trend during childbirth and the postpartum period. The prevalence of all major extragenital complications during labor and the postpartum period showed a downward trend, except diabetes mellitus. The complexity of the analysis lies in the fact that the level of registration of the same pathological conditions during pregnancy and childbirth and in the postpartum period is extremely different. The data obtained indicate the need for improving the early diagnosis of gestosis and statistical recording of complications of pregnancy and childbirth and provide basis for improving the system of monitoring pregnant women and correct diagnosis of pathology in early pregnancy.