Cowpea (Vigna unguiculata(L.) Walp.) yield is strongly influenced by environmental conditions. Average seed yield can decrease to a great extent when drought conditions occur, especially when they prevail during flowering and seed filling periods. Identifying genotypes presenting yield stability is one of the most important breeding goals. Local varieties or crop landraces are genetic resources that, despite exhibiting intermediate yield production capacity, present high yield stability in low-input cropping systems. The objective of this study was therefore to evaluate five selected cowpea landraces originated from different Greek islands under Mediterranean climatic conditions. A complete randomized block design with four replications was used during three consecutive cropping seasons. Many phenological and agronomic traits studied showed statistically significant genotype × experimental year interaction, while there was a strong experimental year effect. Among the landraces studied, local population VG23 from Kythira Island was the most productive under the experimental climatic and soil conditions, while local population VG2 from Lemnos Island was characterized by low seed productivity. Conclusively, our study showed that VG23 landrace is a promising genetic material to be used for seed yield improvement.