The leading role of Italy in the cultivation of durum wheat stimulated intense breeding activities in the country from the beginning of the 20th century, much earlier than in any other country involved in durum wheat production. Older, genetically more heterogeneous landraces were replaced with new, highly productive, superior quality varieties, and this led to an inevitable reduction in the overall genetic diversity among new cultivars, which makes the genetic variability preserved in old cultivars particularly valuable and important. The aim of this paper was to assist future breeding programs by providing a detailed description of the history of durum wheat breeding in Italy and of the changes in yield, quality, and related traits that subsequently occurred, starting from the most diffuse landraces present between 1900 and 1920 up until the present day. The parallel evolution of breeding techniques, breeding goals, and agricultural systems in this period is also described, and some future breeding goals suggested. In the current context of climate change and of rapidly mutating pathogen populations, preserving the yield level through the continuous introduction of new cultivars by exploiting the reservoir of largely unused genetic variation stored in old cultivars and landraces could be as important as increasing grain yield and quality.