We investigated the relationship between dam's pelvic and calf's dimensions with dystocia due to fetopelvic disproportion in the Holstein breed and estimated risk factors and dystocia probability. For this purpose, external pelvic measurements were performed in 402 heifers 15 ± 11 (1–38) days ante-partum and specific conformation measurements were obtained from their calves 1.7 ± 1.2 post-partum. Dystocia was defined as the inability of the heifer to complete parturition spontaneously within 120 min after the appearance of the amnion with normal presentation, position and posture or as having definite obstetrical obstacles within 60 min. Overall and fetopelvic disproportion dystocia incidence was 10.4% and 5.2%, respectively. Heifer measurements mainly influenced overall dystocia, whereas calf conformation was related solely with fetopelvic dystocia. Specifically, heifers with a small pelvis (hip width <49.95 cm, pelvic inlet area <333.2 cm2, pelvic volume <7799.2 cm3) had 2.8 to 3.5 times greater incidence of overall dystocia (19.0–20.8%) compared to heifers with a larger pelvis (incidence of 7.0–7.6%). Regarding calf factors, sex (male calves), body weight, chest circumference and fetlock joint circumference significantly increased the odds of experiencing dystocia due to fetopelvic disproportion compared with female, lighter or smaller calves. In a backward elimination model with independent variables treated as continuous, an area under the ROC curve of 0.66 regarding the prediction of overall dystocia based on heifer pelvic length, and of 0.64 for the prediction of fetopelvic dystocia based on fetlock joint circumference was found. The combination of the two variables in one model improved the ROC area to 0.71 regarding dystocia due to fetopelvic disproportion, reaching acceptable level of discrimination. Our findings indicate that dystocia due to fetopelvic disproportion in heifers is mainly influenced by the fetal side. Additionally, the estimation of pelvic dimensions of the dam before parturition and specific conformation characteristics of the calf during parturition, especially fetlock joint circumference, could aid obstetricians and herdsmen regarding dystocia probability and parturition surveillance.