Based on previous in vitro results that showed reduced biohydrogenation of oleamide by ruminal microbes, this study was conducted to determine whether the addition of oleamide to the diets of dairy cows would enhance the C18:1 concentration in milk. Nine first lactation Holstein cows were fed three diets in a 3 x 3 Latin square replicated three times. Each period lasted 3 wk. The total mixed diets consisted of 42% corn silage and 58% concentrate (dry matter basis) with either no added fat (control), 3.5% high oleic canola oil, or 3.5% oleamide. Dry matter intake was reduced when oleamide was added to the diet but not when canola oil was added. Milk yields were the same for cows fed all three diets. Canola oil reduced fat-corrected milk yield and milk fat concentration, but these were not affected by oleamide. Milk protein concentration was lower for cows fed oleamide than for cows fed canola oil. Milk C18:1 averaged 23.16% of total fatty acids for cows fed the control diet and increased to 35.13% when canola oil was fed. Oleamide further increased C18:1 to 48.16% of total fatty acids in milk. All fatty acids with > or = 16 carbon chain length were reduced by oleamide. Oleamide was more effective than was canola oil in this study at increasing the oleic acid content of bovine milk. Oleamide reduced dietary intake when added at 3.5% of the dietary dry matter but still had no effect on milk yield or milk composition.