To estimate the rates of diabetes complications and revascularization procedures among people with diabetes who have experienced homelessness compared with a matched cohort of nonhomeless control subjects. A propensity-matched cohort study was conducted using administrative health data from Ontario, Canada. Inclusion criteria included a diagnosis of diabetes and at least one hospital encounter between April 2006 and March 2019. Homeless status was identified using a validated administrative data algorithm. Eligible people with a history of homelessness were matched to nonhomeless control subjects with similar sociodemographic and clinical characteristics. Rate ratios (RRs) for macrovascular complications, revascularization procedures, acute glycemic emergencies, skin/soft tissue infections, and amputation were calculated using generalized linear models with negative binomial distribution and robust SEs. Of 1,076,437 people who were eligible for inclusion in the study, 6,944 were identified as homeless. A suitable nonhomeless match was found for 5,219 individuals. The rate of macrovascular complications was higher for people with a history of homelessness compared with nonhomeless control subjects (RR 1.85, 95% CI 1.64-2.07), as were rates of hospitalization for glycemia (RR 5.64, 95% CI 4.07-7.81) and skin/soft tissue infections (RR 3.78, 95% CI 3.31-4.32). By contrast, the rates of coronary revascularization procedures were lower for people with a history of homelessness (RR 0.76, 95% CI 0.62-0.94). These findings contribute to our understanding of the impact of homelessness on long-term diabetes outcomes. The higher rates of complications among people with a history of homelessness present an opportunity for tailored interventions to mitigate these disparities.