Transition-metal-catalysed C–H functionalization has emerged as a powerful approach for the transformation of organic molecules due to its high atom and step economy. Palladium-catalysed intermolecular C–H annulation of aryl halides, especially those involving annulation of a five-membered C,C-palladacycle with coupling reagents, have attracted considerable attention in the past decades. This review summarizes the progress on palladium-catalysed intermolecular C–H annulation of aryl halides with various aromatic ring precursors. Mechanistically, five-membered C,C-palladacycles as intermediates are involved in the majority of reactions.