Two experiments were conducted to study the effects of feeding legume silages and providing supplemental vitamin E in concentrates on the oxidative stability of milk. In experiment 1, six multiparous Holstein-Friesian cows were offered 1 of 6 silage treatments in a cyclical changeover-design experiment, with four 4wk periods. The silages were grass, red clover, white clover, alfalfa, grass and red clover mixture (50:50 on a DM basis), and grass and white clover mixture (50:50 on a DM basis). In experiment 2, 8 cows were used in a changeover-design experiment with three 4-wk periods. The 4 treatments were a factorial combination of forages (grass silage or red clover silage) and supplemental vitamin E in the form of all-rac-α-tocopheryl acetate (29 or 290 IU/kg of DM in the concentrate). All forages were offered ad libitum and a flat rate of concentrates (8 kg/d) was fed in both experiments. Red clover silage led to significantly higher forage intakes, milk yields, and milk protein percentage in experiment 2, which was in agreement with results from experiment 1. There was no effect of vitamin E on feed intake, milk production, or milk fat and protein percentage. Red clover silage also led to significant changes in milk fatty acid profiles, particularly increased levels of polyunsaturated fatty acids. Milk samples were stored at 4°C and 20°C and analyzed for α-tocopherol and thiobarbituric acid reactive substances at intervals to determine oxidative stability. Diets based on red clover and alfalfa silages were associated with more rapid loss of α-tocopherol and increased production of thiobarbituric acid reactive substances during the storage of milk in comparison with diets based on grass silage. The increased oxidative deterioration of milk produced from cows fed red clover silage was avoided by vitamin E supplementation.