Milk oligosaccharides (MOs) are complex carbohydrates with multifunctional health benefits for the neonate. Poor reproductive performance in primiparous gilts limits their productivity. Changes in the structure and abundance of porcine MO (PMOs) through lactation with parity remains unknown and may explain superior new-born growth in litters from multiparous sows relative to gilts. We report 55 PMOs structures, of which 25 are new (17 sialylated and 8 neutral). Their incidence in gilt and sow colostrum was almost identical (53 vs. 54), but not in transitional milk (48 vs. 53) nor mature milk (41 vs. 47). These PMOs including neutral-, sialyl- and fucosyl- MOs in colostrum were more abundant in the gilt than the sow, but always decreased during lactation. Structural diversity decreased, although fucosylated MO were conserved. In conclusion, high diversity and levels of MO in porcine milk is parity dependent. Given the similarity between porcine and human MO profiles, our findings may help define key roles for MOs as potential dietary additives to improve growth of neonates from first pregnancies in both human and sows.