Cowpea (Vigna unguiculata) is a robust legume; nevertheless, yield is always affected by drought, especially when it occurs during reproductive growth and seed filling. Considered a key crop in the effort to attain food security, and a suitable crop for a scenario of climate change, modern disregard for cowpea landraces is particularly detrimental as it causes genetic variability loss, compromising breeding efforts. To contribute to the evaluation of the cowpea germplasm, four Portuguese landraces (L1, L2, L3, L4) were compared with a commercial variety (CV) to evaluate their physiological responses to terminal drought and their inter-variation on productivity, under semi-controlled conditions. Despite no differences in relative water content (RWC) between the CV and the landraces under water deficit (WD), differences in leaf water potential (Ψ) defined the CV as having an isohydric control of stomata in contrast with anisohydric control for landraces. There was an identical decrease in the photosynthetic rate for all plants under stress, caused by both stomatal and non-stomatal limitations, namely, damages at the level of photosystem II as indicated by fluorescence measurements. Instantaneous water use efficiency (iWUE) was improved with stress in L1 and L3. Maintenance of higher relative chlorophyll content for longer periods in the CV revealed a stay-green phenotype. The slim differences observed in terms of stomatal control, iWUE and progression of senescence between the CV and the landraces under WD led to quite important differences in terms of productivity, as inferred from improved yield (number of pods and number of grains per plant). This is a clear result of pragmatic on-farm selection. On one hand it shows that small differences in stomatal responses or water saving strategies under WD may lead to desirable outcomes and should therefore be considered during breeding. On the other hand, it suggests that other traits could be explored in view of drought adaptation. These results highlight the need to preserve and characterize as many genetic pools as possible within a species.