Simple SummaryLongevity, or the length of a cow’s productive life, is important in terms of profitability, animal welfare and environmental sustainability. In genetic evaluations, interest focuses on functional longevity, defined as a cow’s ability to avoid forced culling, an ability that increases the possibility of voluntary disposal based on economic criteria. Longevity is affected by several non-productive functional traits, among them those related to calving performance: calving ease (dystocia) and perinatal calf mortality (stillbirth). Parturition is a critical event in a cow’s life that has a number of different short- and long-term consequences. In the Polish Holstein-Friesian population, the incidence of dystocia and stillbirth is within the lower range of frequencies found in other dairy cattle populations. Our research showed that both traits affect functional longevity. Difficult calvings occur more frequently in heifers and increase the risk of involuntary culling more than in later parturitions. Additionally, a higher risk of culling is related to birth of a male calf. Moreover, the negative impact of calf mortality on longevity is also more pronounced in primiparous cows and in the case of delivery of male calves. Reducing the incidence of calving problems and perinatal mortality may improve the longevity of dairy cows.Longevity is one of the functional traits that considerably affect dairy herd profitability. A Weibull proportional hazards model was used to evaluate the impact of difficult calvings and calf stillbirths on cow functional longevity, defined as length of productive life corrected for milk production. The data for analysis comprised calving ease and calf mortality scores of 2,163,426 calvings, 34.4% of which came from primiparous cows. The percentage of male calves was 53.4%. Calving ease was scored as “without assistance” (34.44%), “with assistance” (62.03%), “difficult—hard pull” (3.39%), and “very difficult, including caesarean section” (0.14%). Calf mortality scores were “live born” (94.21%) and “stillborn or died within 24 h” (5.79%). The Weibull proportional hazards model included classes of calving ease or calf mortality scores × parity (1, ≥2) × sex of calf as time-dependent fixed effect. The model also included time-dependent fixed effects of year × season, parity × stage of lactation, annual change in herd size, fat yield and protein yield, time-independent fixed effect of age at first calving, and time dependent random herd × year × season. In first-parity cows, very difficult birth of a bull or heifer increased the relative risk of culling, respectively, 2.18 or 1.26 times as compared with calving without assistance. In later parities, the relative risk of culling related to very difficult calving was 2.0 times (for male calves) and 1.33 times (for female calves) higher than the relative risk of culling associated with calving without assistance. Calf mortality showed a negative impact on longevity in both heifers and cows. First-parity stillbirth increased the relative risk of culling depending on sex of calf by 18% in females and by 15% in males; in later parities the increase of the relative risk of culling was lower (by 7% for females, 9% for males). Difficult calvings and their consequences, especially in primiparous cows, may negatively influence dairy herd profitability by reducing the length of cows’ productive life.