The design and development of phosphorus based macrocycles containing one or more other heteroatoms is of crucial importance for the enhancement of modern synthetic chemistry. In recent years focus on phosphorus based macromolecules has led to intriguing and innovative structures with a variety of applications, including photophysical and host–guest properties, and in organic synthesis. This article summarizes the recent advancements in the synthesis of macrocycles that consist of organophosphorus–chalcogen (P–E, PE; E = O, S, Se) and organophosphorus–pincer based macrocyclic ligands and their transition metal complexes with emphasis given to synthetic methodologies. The reactions involve the modification of simple macrocycles with phosphorus sources or phosphorus-based chalcogenating reagents. Transition metal complexes of phosphine-based macrocyclic pincer ligands and their reactivity are also included.