The use of multiple-center intramolecular H-bonds for the efficient construction of macrocycles of varying structures and functions is among the newest and the most noteworthy additions to the toolbox for macrocycle synthesis. This strategy has allowed the creation of sizable interior cavities as small as 2.8 Å and as large as 15 Å in radius in these H-bonded macrocycles with a number of them expressing tailor-made functions. While concentrating on our recent contributions to this fast-growing field, we will further summarize the latest advances on the design, synthesis, structure and function of these shape-persistent H-bonded macrocyclic foldamers that have helped to create a whole new dimension of scientific research, markedly expanding both the structural and functional repertoires of shape-persistent macrocycles.