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Athlete health is essential for sustained performance in professional sport, with injuries and illnesses limiting both individual and team success. Although athlete monitoring is widely used to support load and recovery management and reduce injury risk, evidence linking training load, well-being and health outcomes in professional basketball is inconsistent. Holistic monitoring approaches may enhance the understanding of load-related health dynamics. Therefore, this study aimed to investigate the associations between internal load, sleep, and physical and mental well-being and the occurrence of injury and illness in professional male basketball players across a competitive season. In this prospective observational study (German Clinical Trials Register ID: DRKS00032713; registered 19 October 2023), 16 professional male basketball players were monitored over a 31-week competitive season using a software application (Prevention Management Tool, PMT) provided by the German Accident Insurance for professional team sports. Structured injury and illness surveillance was conducted throughout the study period. Internal load was assessed 30 min after each training session and match using the session rating of perceived exertion (sRPE) method. In addition to sleep duration, PMT-integrated athlete self-reported measures collected each morning assessed sleep quality, physical and mental well-being using 11-point Likert scales (0–10). Linear mixed-effects models were used to investigate the associations between internal load, sleep and well-being and the occurrence of injury and illness. A total of 3,454 athlete records were included in the analyses, corresponding to a completion rate of 88.9%. Mean weekly internal load derived from sRPE was 3,873 ± 1,524 arbitrary units. Mean daily sleep duration was 8.16 ± 1.17 h. Mean scores for sleep quality, physical well-being, and mental well-being were 7.59 ± 1.34, 7.78 ± 1.27, and 7.76 ± 1.28, respectively. The cumulative season incidence rates were 1.31 for acute injuries, 0.50 for overuse injuries, and 2.06 for illnesses. Higher internal load and lower sleep quality were associated with reduced physical and mental well-being. Lower physical well-being was significantly associated with illness occurrence (P < .001, η²ₚ = 0.03), whereas physical and mental well-being were not associated with injury occurrence. Higher internal load and lower sleep quality were associated with reduced well-being in professional male basketball players. Decreased physical well-being was associated with illness occurrence, supporting its relevance as a potential early indicator within athlete health monitoring frameworks.