Abstract: Long term investigations on the combined effects of tillage systems and other agronomic practices such as mineral N fertilization under Mediterranean conditions on durum wheat are very scanty and findings are often contradictory. Moreover, no studies are available on the long term effect of the adoption of conservation tillage on grain yield of maize and sunflower grown in rotation with durum wheat under rainfed Mediterranean conditions. This paper reports the results of a 20-years experiment on a durum wheat-sunflower (7 years) and durum wheat–maize (13 years) two-year rotation, whose main objective was to quantify the long term effects of different tillage practices (CT = conventional tillage; MT = minimum tillage; NT = no tillage) combined with different nitrogen fertilizer rates (N0, N1, N2 corresponding to 0, 45 and 90 kg N ha−1 for sunflower, and 0, 90 and 180 kg N ha−1 for wheat and maize) on grain yield, yield components and yield stability for the three crops. In addition, the influence of meteorological factors on the interannual variability of studied variables was also assessed. For durum wheat, NT did not allow substantial yield benefits leading to comparable yields with respect to CT in ten out of twenty years. For both sunflower and maize, NT under rainfed conditions was not a viable options, because of the unsuitable (i.e., too wet) soil conditions of the clayish soil at sowing. Both spring crops performed well with MT. No significant N × tillage interaction was found for the three crops. As expected, the response of durum wheat and maize grain yield to N was remarkable, while sunflower grain yield was not significantly influenced by N rate. Wheat yield was constrained by high temperatures in January during tillering and drought in April during heading. The interannual yield variability of sunflower was mainly associated to soil water deficit at flowering and air temperature during seed filling. Heavy rains during this latter phase strongly constrained sunflower grain yield. Maize grain yield was negatively affected by high temperatures in June and drought in July, this latter factor was particularly important in the fertilized maize. Considering both yield and yield stability, durum wheat and sunflower performed better under MT and N1 while maize performed better under both CT and MT and with N2 rates. The results of this long term study are suitable for supporting policies on sustainable Mediterranean rainfed cropping systems and also for cropping system modelling.