Gambling problems are often associated with homelessness and linked to elevated psychiatric morbidity and homelessness chronicity. We performed a systematic review and meta-analysis on prevalence rates of problem gambling (PG) and gambling disorder (GD) in homeless people. Following PRISMA guidelines, we searched databases Medline, Embase and PsycINFO from inception of databases to 4th may 2021. We included studies reporting prevalence estimates on clinical gambling problems in representative samples of homeless people based on standardized diagnostics. Risk of bias was assessed. A random effects meta-analysis was performed, and subgroup analyses based on methodological characteristics of primary studies were conducted. We identified eight studies from five countries, reporting information on 1938 participants. Prevalence rates of clinically significant PG and GD ranged from 11.3 to 31.3%. There was evidence for substantial heterogeneity with I2= 86% (95% CI 63–97%). A subgroup of four low risk of bias studies displayed a significantly lower results ranging from 11.3 to 23.6%. Additionally, high rates of subclinical problem gambling were reported (11.6–56.4%). At least one in ten homeless persons experiences clinically significant PG or GD. Social support and health care services for the homeless should address this problem by implementing models for early detection and treatment.Supplementary InformationThe online version contains supplementary material available at 10.1007/s10899-022-10140-8.