This study analyzes 174 tank milk samples taken from 89 commercial farms located all along the Cantabrian Coast (Green Spain). Sampling was performed in two periods: autumn 2016 and spring 2017. A survey was carried out for every day of sampling to record the average lactating dairy cow production and its diet composition. For each sample, the fatty acid (FA) profile (49 FA plus its main relationships) and nine fat-soluble antioxidant (FSA) profiles (retinol (vitamin A), α- and Υ-tocopherol (vitamin E), all-trans-β-carotene, 9-cis-β-carotene, 13-cis-β-carotene, lutein, zeaxanthin, and β-cryptoxanthin) were determined. The milk production varied between 7.3 and 45.9 liters per cow per day, highlighting the diversity found among production systems. The milk fat content ranged from 2.64% to 4.38% and the protein content from 2.87% to 3.56%. Regarding the fatty acids profile, the percentage of saturated fat varied between 59.95% and 75.99%. The linolenic acid content fluctuated between 0.21 and 1.31 and rumenic acid ranged from 0.20 to 2.47 (g 100 g−1 total FA). The most important correlations between diet and milk FA were always related to the content of fresh grass and total forage (which is defined by both fresh and conserved forage derived from fresh grass (GCF)) in the diet. The content of vaccenic acid, linolenic acid, total omega-3, rumenic acid, and total CLA isomers showed the highest correlation with the proportion of fresh grass in the diet. The antioxidant contents were also highly variable, although correlations with dietary components were lower. The highest correlations were between total forage content (fresh grass (FG) plus GCF) and lutein, all-trans-β-carotene, and 13-cis-β-carotene. Diets without fresh grass had lower omega-3 content, CLA, vaccenic acid, lutein, all-trans-β-carotene, and 13-cis-β-carotene.