Crossbreeding is a strategy to counter the declining fertility, resilience, and longevity of purebred Holstein (Ho) cows. However, little is known of the effects of long-term systematic rotational crossbreeding on milk technological properties and cheese yield (CY). In this study, we compared the individual milk composition, milk coagulation properties (MCP), and CY of 468 purebred Ho and 648 crossbred (CR) cows obtained from two 3-breed rotational crossbreeding systems using Viking Red (VR), Montbéliarde (Mo), and Ho sires over 4 generations. Individual milk samples were collected once from 1,116 primiparous and multiparous cows kept in 2 dairy herds, raised for the production of Grana Padano (high milk yield, total mixed ration based on corn silage) and Parmigiano Reggiano (moderate milk yield, only dry feeds) cheeses. In both herds, a 3-breed rotational mating system was used in which Ho cows were first inseminated with VR, whereas Mo and Ho semen was used in the subsequent generations. In one herd, the sequence Mo-VR-Ho was also used. Individual milk samples were analyzed for milk composition, single-point MCP, and parameters for modeling curd firming over time, whereas CY and milk nutrient recovery in the curd were assessed through a laboratory cheese-making procedure. Compared with Ho, CR cows produced 5.8% less milk, which had comparable fat but greater protein and casein contents and lower lactose contents and somatic cell scores. Milk from CR cows tended to reach a curd firmness of 20 mm more quickly and exhibited greater curd firmness at 45 and 60 min from rennet addition. Holstein and CR cows yielded milk with similar CY and recovery in the curd traits. The milk fat content, somatic cell scores, curd firmness traits, and CY of CR cows relative to the Ho cows differed in the 2 herds, and the favorable effects on the CR cows were more evident in the herd with the greatest milk yield and the worst MCP traits. Crossbred cows of the 4 generations performed similarly, with the exception of the better MCP of the milk from firstgeneration CR cows. The 2 rotational systems using different sire-breed sequences also performed similarly. In summary, both rotational crossbreeding programs exhibited some advantage over the Ho purebred breeding system in terms of milk composition and MCP but not CY. Future research is needed to investigate the interactions between crossbreeding schemes and dairy systems.