Under the obstetrical dilemma hypothesis, sexual dimorphism in pelvic shape is a solution to accommodate high fetopelvic constraints. It is therefore unclear why chimpanzees display a human-like pattern of pelvic sexual dimorphism despite having easier births enabled by small neonates and capacious pelvic canals. Here we reassessed chimpanzee fetopelvic fit using three-dimensional simulations, revealing a similarly constricted midpelvis as in humans, with even narrower outlet dimensions. Geometric morphometric analyses confirm that female chimpanzees have larger pelvic canals than males despite a smaller body size and a morphology that maximizes pelvic dimensions favourable for parturition, particularly in smaller-bodied individuals. Together with evidence for increased neurological immaturity at birth relative to monkeys, our findings imply substantial obstetric constraints in chimpanzees and possibly other apes. We therefore propose that difficult birth did not arise abruptly in Homo with increasing encephalization but evolved gradually through a series of obstetric compromises from an already constricted birth canal shared across anthropoid primates. Specifically, we propose that obstetric selection pressures exacerbated incrementally with the stiffening of the symphysis that accompanied body size increase in hominoids, while subsequent adaptations to bipedalism shortened the ilium. The resulting contorted birth canal required obligatory fetal rotation, thus greatly increasing birth difficulty.