The aim of the present study was to compare the effect of dietary tannins on cow cheese quality in 2 different grazing seasons in the Mediterranean. Two experiments were performed on 14 dairy cows reared in an extensive system. The first experiment took place in the wet season (WS), and the second experiment took place in the dry season (DS). In the WS and DS experiments, cows freely grazed green pasture or dry stubbles, respectively, and the diet was supplemented with pelleted concentrate and hay. In both experiments, the cows were divided into 2 balanced groups: a control group and a group (TAN) receiving 150 g of tannin extract/head per day. After 23 d of dietary treatment, individual milk was collected, processed into individual cheeses, and aged 25 d. Milk was analyzed for chemical composition, color parameters, and cheesemaking aptitude (laboratory cheese yield and milk coagulation properties). Cheese was analyzed for chemical composition, proteolysis, color parameters, rheological parameters, fatty acid profile, and odor-active volatile compounds. Data from the WS and DS experiments were statistically analyzed separately with an analysis of covariance model. In the WS experiment, dietary tannin supplementation had no effect on milk and cheese parameters except for a reduced concentration of 2-heptanone in cheese. In the DS experiment, TAN milk showed lower urea N, and TAN cheese had lower C18:1 trans-10 concentration and n-6:n-3 polyunsaturated fatty acid ratio compared with the control group. These differences are likely due to the effect of tannins on rumen N metabolism and fatty acid biohydrogenation. Dietary tannins may differently affect the quality of cheese from Mediterranean grazing cows according to the grazing season. Indeed, tannin bioactivity on rumen metabolism seems to be enhanced during the dry season, when diet is low in protein and rich in acid detergent fiber and lignin. The supplementation dose used in this study (1% of estimated dry matter intake) had no detrimental effects on cheese yield or cheesemaking parameters. Also, it is unlikely that sensorial characteristics would be affected by this kind of dietary tannin supplementation.