The relationships between the fatty acid (FA) composition in forage and milk (F&M) from different dairy systems were investigated. Eighty milk samples and 91 forage samples were collected from 40 farms (19 organic, 11 pasture and 10 conventional) in the Netherlands, during winter and summer. The FA profiles of F&M samples were measured with gas chromatography. The results showed that the F&M of organic farms were significantly differentiated from the F&M of other farms, both in summer and winter. The differences are likely due to the different grazing strategies in summer and different forage composition in winter. The Pearson's correlation results showed the specific relationship between individual FAs in forages and related milk. A PLS-DA model was applied to classify all milks samples, resulting in 87.5% and 83.3% correct classifications of training set and validation set.