Changes in elements of courtship behaviour can influence sexual isolation between species. Large-scale analyses of changes, including loss and gain of courtship elements, across a relatively complete phylogenetic group are rare but needed to understand the significance of such changes, for example whether the gain and loss of courtship elements are essentially arbitrary or equally reversible. In most species of Drosophila, courtship, including singing, mainly occurs before mounting as pre-mounting courtship. The Drosophila montium species group is unusual because loss of pre-mounting courtship and gain of post-mounting one has been detected in this group. Here we provide an extensive analysis on the courtship repertoire and songs of 42 species in this group. Synchronously captured video and audio recordings were analysed to describe courtship patterns and male courtship songs and changes were analysed in a phylogenetic context. Ancestral state reconstruction suggests that a gain of post-mounting courtship singing at the ancestor of this species group has been accompanied with a concurrent decrease in the incidence of pre-mounting courtship singing and has led to subsequent further decrease and eventually complete loss of pre-mounting courtship song in several lineages. Alongside this evolutionary trend towards post-mounting courtship, sine song and a special type of “high pulse repetition song” have become more widely used for courtship during species diversification in the montium group. It is likely that the elaboration of post-mounting courtship behaviours is associated with changes in the relative importance of pre- and post-mounting components of mating systems, such as sperm competition or cryptic female choice.