Lentil (Lens culinaris Medik.) is widely known among grain legumes for its high nutritional quality, playing an important role in enhancing Mediterranean farming systems as a sustainable crop. Field experiments comparing 121 lentil accessions (microsperma and macrosperma types from different countries) were conducted in a semi-arid environment of south Italy over two growing seasons (2016/2017 and 2017/2018). Their agronomic performance was determined, focusing on phenological, morphological, productive, and qualitative variability. Changes in rainfall and temperatures affected the agronomic traits, especially yield components. In both years, the average grain yield (GY) (2.31 and 2.22 t ha−1, respectively) was above the threshold of 2 t ha−1. Consistent yield exceeding the field average in both growing seasons revealed the superiority of accessions from Egypt, Cyprus, Algeria, Nepal, and Tunisia. Moreover, microsperma yielded more (+0.31 and +0.41 t ha−1 in the first and second year, respectively) than macrosperma accessions. Flowering (DASF—days after sowing to flowering) and thousand seed weight (TSW) appeared to be the most important traits related to grain yield. Flowering earliness seems to act as a mechanism for overcoming abiotic stresses. The analysis of yield components revealed a different productive determinism within the two subspecies. As also highlighted by the Principal Component Analysis, microsperma accessions presented on average a significantly higher number of pods per plant (PP) and seeds per pod (SP), despite the considerable variability among countries of origin. The results showed phenological and morphological variability among genotypes, which should be taken into account in view of future selection programs focused on obtaining lentil ideotypes suitable for the Mediterranean environment.