Bulk tank milk from 28 dairy farms was sampled every second month for 2 yr to assess the effects of grassland management, production system and season on milk fatty acid (FA) composition, concentrations of fat-soluble vitamins, Se, and milk sensory quality. Grassland management varied in terms of time since establishment. Short-term grassland management (SG) was defined as establishment or reseeding every fourth year or more often, and long-term grassland management (LG) was defined as less frequent establishment or reseeding. Fourteen organic (ORG) dairy farms with either short-term or long-term grassland management were paired with 14 conventional (CON) farms with respect to grassland management. Within ORG farms, SG farms differed from LG farms in herbage botanical composition, but not in concentrate FA concentrations, dry matter intake, or milk yield. Within CON farms, herbage composition, concentrate FA concentrations, dry matter intake, and milk yield showed no or insignificant variations. The ORG farms differed from CON farms in herbage botanical composition, concentrate FA concentrations, concentrate intake, and milk yield. Compared with ORG-LG farms, ORG-SG farms produced milk fat with higher proportions of C10:0 and C12:0 associated with higher herbage proportions of legumes (Fabaceae) and lower proportions of other dicotyledon families. Compared with milk from CON farms, milk fat from ORG farms had higher proportions of most saturated FA and all n-3 FA, but lower proportions of C18:0 and C18:1 cis-9 associated with higher forage proportion and differences in concentrations of FA in concentrates. Compared with the outdoor-feeding periods, the indoor feeding periods yielded milk fat with higher proportions of most shortchain and medium-chain FA and lower proportions of most C18-FA associated with grazing and higher forage proportions. Milk concentrations of α-tocopherol and β-carotene were lower during the grazing periods. Inclusion of fishmeal in organic concentrates may explain higher Se concentrations in organically produced milk. Milk sensory quality was not affected in this study. In conclusion, grassland management had minor effects on milk composition, and differences between ORG farms and CON farms may be explained by differences in concentrate intake and concentrate FA concentrations. Milk produced on ORG farms versus CON farms and milk produced during the outdoor versus indoor feeding periods had potential health benefits due to FA composition. In contrast, the higher milk-fat proportions of saturated FA in milk from ORG farms may be perceived as negative for human health.