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Total fatty acid and sn-2 fatty acid compositions, and triacylglycerol (TAG) species in 130 sow colostrum, 100 sow milk, and 22 piglet formula samples were analyzed in the present study. Significant differences were found in concentrations of medium chain-saturated fatty acids (MC-SFAs) and distributions of palmitic acid (P) and oleic (O)/linoleic (L) acid. The levels of MC-SFAs in sow colostrum and sow milk fats (2.4–3.1%) were significantly lower than those in piglet formulas (7.9–27.2%). Approximately 63% of palmitic acid was located at the sn-2 position in both sow colostrum and milk fats, which was significantly higher than in piglet formula fats (21.1–39.1%). Correspondingly, only 17.8–28.3% of oleic and linoleic acids were at the sn-2 position in sow milk fats, contributing to their typical triacylglycerol structure in sow colostrum and milk, whose palmitic acid connected to the sn-2 position and unsaturated fatty acids located at the sn-1,3 positions. Sow colostrum, milk, and piglet formulas were notably distinguished into three groups based on their fatty acids and TAGs, among which triacylglycerols were the most differentiated index. A total of 51 TAG species (including their isomers) differed significantly between sow colostrum and milk and piglet formulas. OPL and OPO were the most important differentiating TAGs. The large amount of sn-2 esterified palmitic acid plays a key role in improving the absorption of fat and calcium. The results provide suggestions for design of sow milk fat equivalents.