Simple Summary Since 2013, a Chilean law regulates the welfare of farm animals. Despite advances in scientific knowledge and legislation, many farms use management practices that can be detrimental to animals. The objectives of this study were to describe common management practices that may affect the welfare status of unweaned dairy calves and identify factors associated with diarrhea and respiratory disease. We visited 29 dairy farms and collected information on management practices, environment, and animal health. Management practices identified as risk factors for poor calf welfare were: reliance on the mother to provide colostrum, use of restrictive milk feeding (<4 L/day), disbudding performed with no pain control, and lack of appropriate euthanasia protocols. Factors associated with diarrhea were: frequency of bed cleaning, calf cleanliness score, type of milk, and herd size. Factors associated with respiratory disease were: calf cleanliness score, pen space allowance, and colostrum quality evaluation. Showing critical points that impact the health and welfare of dairy calves facilitates the implementation of improvement strategies. This study aimed to describe management practices that may compromise the welfare of unweaned dairy calves on 29 dairy farms in Chile, and identify factors associated with diarrhea and respiratory disease (n = 700 calves). Evaluations were divided into protocol-, facility-, and animal-based measurements. Calf diarrhea and respiratory disease data were analyzed using logistic regression models. Management practices identified as risk factors for poor calf welfare were: relying on the mother to provide colostrum (48.0% of the farms); using restrictive milk feeding (65.5%), and unpasteurized waste milk (51.7%); giving water after 30 days of age (17.2%); disbudding without analgesia (89.6%) or anesthesia (79.3%); lacking euthanasia protocols (61.5%). Factors significantly (p< 0.05) associated with increased odds of diarrhea were: cleaning the calves' bed once a week and 2-3 times a week compared with every day, using milk replacer and untreated waste milk compared with treated waste milk (pasteurized or acidified), animals scored dirty in the calf cleanliness score compared with clean animals, and greater herd size. Factors significantly associated with increased odds of respiratory disease were: less pen space allowance (<1.8 m(2)), farms that did not check colostrum quality, and animals that scored dirty and moderately dirty compared with clean calves. These results suggest the need to improve specific management practices associated with reduced welfare and health in dairy calves in Chile.