Adolescent gay/bisexual men exhibit the highest prevalence of undiagnosed HIV infections. Ascertaining antecedents of behaviorally acquired HIV infections among adolescent gay/bisexual men can be challenging; however, these challenges can be overcome through the utilization of secondary data, such as the Youth Risk Behavior Survey. Syndemics theory suggests that HIV infections are not a singular phenomenon; instead, many infections occur at the intersection of syndemic factors, such as substance use, violence, and mental health. Our objective is to describe and synthesize research methods of secondary data analyses that examine syndemic factors in relation to HIV risk behavior outcomes among subsamples of adolescent gay/bisexual men. Following Preferred Reporting Items for Systematic Reviews and Meta-Analyses guidelines, PubMed, Cumulative Index to Nursing and Allied Health Literature, and PsycInfo were systematically searched. Inclusion criteria were (a) peer-reviewed Youth Risk Behavior Survey secondary data analyses conducted in the United States after 1991, (b) subsamples with adolescent gay/bisexual men, (c) one or more syndemic factor(s), and (d) one or more HIV risk behavior outcome(s). We used the National Institutes of Health Quality Assessment Tools for quality appraisal. Of 1,036 citations retrieved, nine studies met inclusion criteria. Results included using logistic regression analysis and data from 2015 to 2017 in six studies and underpinnings with minority stress theory in four studies. Eight studies omitted race/ethnicity in subsamples and six grouped lesbians with adolescent gay/bisexual men. Seven studies examined substance use, six examined violence, and five examined mental health. Condom use and number of partners were the most studied HIV risk behavior outcomes in four studies, whereas intercourse in the last 3 months was an outcome in only one study. Protective factors were not present. Limitations found the need to highlight better inclusion of race/ethnicity and sexual orientation. Adding contemporary survey items is also necessary, such as nonbinary sex and gender identity, access to HIV prevention (condoms, HIV testing, and preexposure prophylaxis), and experiences with stigma, to elucidate risk behaviors among populations disproportionately affected by HIV infections, including Blacks/African Americans and Hispanics/Latinos.