Background and aims – In Cyperaceae, the single-ovuled, usually triangular gynoecia are widely considered to have a basic number of three carpels, often reduced to two, resulting in dimerous pistils. However, laterally flattened dimerous pistils cannot be explained by any existing carpel reduction theories, because a single stigma in median position replaces the two adaxial stigmata. This paper presents a comparative study of the ontogenetic and anatomical adaptations facilitating the origin of new pistil forms in Cyperoideae, focusing on modified gynoecia. It includes a re-evaluation of Blaser’s (1941) anatomical studies in Cyperaceae. We aim to test Blaser’s hypothesis that is based on an acropetal developmental model of the floral vasculature and the general Cyperoid ontogenetic model of Vrijdaghs et al. (2009), which states that cyperoid ovaries originate from an annular primordium. Methods – SEM, dark field and phase contrast microscopy. Key Results – All cyperoid pistils studied develop according to a cyperoid floral ontogenetic pattern, in which carpel primordia are congenitally fused. In Pycreus sanguinolentus (and other species), separate procambial initiation zones were observed in both the flower receptacle and separate floral primordia, which connect (or not) at later developmental stages. Conclusions – The presence of an annular ovary primordium instead of individual carpel primordia, combined with the bidirectional development of the pistil vasculature liberate the developing gynoecium from the structural constraints proper to a typical carpellate organisation. Procambial initiation zones in the receptacular vascular plexus and in individual floral primordia constitute the basis for the formation of a flexible vascular system in cyperoid flowers. Moreover the development of the ovary and ovule are decoupled. Consequently, in Cyperoideae the acquired developmental freedom of the pistil resulted in various adaptations.