Osteomyelitis is the leading cause of total carcass condemnation in finishing pigs in Portugal, causing significant economic losses in swine production. The present study sought to determine a possible link between osteomyelitis in pig carcasses, pre-slaughter factors, and concomitant post-mortem inspection findings. For this purpose, meat inspection data were collected from 100,489 finishing pigs slaughtered in a northern Portuguese abattoir. Information regarding total carcass condemnation, slaughter season, origin, sex, tail-biting lesions, and husbandry invasive procedures (tail docking and teeth resection) was collected. The main cause of total carcass condemnation was osteomyelitis (61.03%). A total of 36.16% of osteomyelitis cases were present in the anterior region and 52.20% in the posterior region. In the anterior region, 94.78% of osteomyelitis cases were in the mandibular bone. Pigs with clipped teeth and carcasses with pleurisies were associated with a higher occurrence of osteomyelitis (p = 0.00262 and p < 0.0001, respectively). Second- and third-grade tail-biting lesions were also linked to a higher occurrence of osteomyelitis (p = 0.00128 and p < 0.0001, respectively). Slaughter inspection and monitoring procedures should be revised to better assess welfare factors and correlate management practices with the occurrence of osteomyelitis in pig carcasses.