HIV continues to be a critical health issue for sexual minority men (SMM) in the USA. Chronic pain is common in individuals with HIV, including older SMM, and is associated with substance use behaviors. This cross-sectional study sought to address a gap in the literature by characterizing interrelationships among chronic pain, substance use disorders (SUDs), medication adherence, and engagement in HIV care among older (≥50) SMM living with HIV and chronic pain (N = 63). The unadjusted relationship between an opioid use disorder and pain indicated that participants with an opioid use disorder reported higher pain ratings than those without. Presence of alcohol use disorder was significantly associated with missed HIV-care appointments due to chronic pain or substance use, showing that individuals with an alcohol use disorder reported more missed appointments in the past year. Higher pain was significantly associated with the same missed appointments variable, such that those reporting higher pain ratings also reported more missed appointments in the past year. These findings provide preliminary evidence of the interrelationships among chronic pain, SUDs, and engagement in HIV care among older SMM living with HIV and suggest that pain management in this population might support fuller engagement in HIV care.