In Mediterranean climates soil water deficit occurs mainly during the spring and summer, having a great impact on cereal productivity. While previous studies have indicated that the grain yield (GY) of triticale is usually higher than bread wheat (Triticum aestivum L.), comparatively little is known about the performance of these crops under water-limited conditions or the physiological traits involved in the different yields of both crops. For this purpose, two sets of experiments were conducted in order to compare a high yielding triticale (cv. Aguacero) and spring wheat (cvs. Pandora and Domo). The first experiment, aiming to analyze the agronomic performance, was carried out in 10 sites located across a wide range of Mediterranean and temperate environments, distributed between 33°34' and 38°41' S. The second experiment, aiming to identify potential physiological traits linked to the different yields of the two crops, was conducted in two Mediterranean sites (Cauquenes and Santa Rosa) in which crops were grown under well-watered (WW) and water-limited (WL) conditions. The relationship between GY and the environmental index revealed that triticale exhibited a higher regression coefficient (Finlay and Wilkinson slope), indicating a more stable response to the environment, accompanied by higher yields than bread wheat. Harvest index was not significantly different between the two cereals, but triticale had higher kernels per spike (35%) and 1000 kernel weight (16%) than wheat, despite a lower number of spikes per square meter. The higher yield of triticale was linked to higher values of chlorophyll content, leaf net photosynthesis (An), the maximum rate of electron transport (ETRmax), the photochemical quantum yield of PSII [Y(II)] and leaf water-use efficiency. GY was positively correlated with Ci at anthesis and Δ13C in both species, as well as with gs at anthesis in triticale, but negatively correlated with non-photochemical fluorescence quenching and quantum yield of non-photochemical energy conversion at grain filling in wheat. These results revealed that triticale presented higher photosynthetic rates that contributed to increase plant growth and yield in the different environments, whereas wheat showed higher photoprotection system in detriment of assimilate production.