Background: Emergency Medical Services (EMS) is an important resource that interacts with our most vulnerable patients during transport home after hospital discharge. EMS providers may be appropriately situated to support the transition of care to the home environment. Objectives: This study aimed to determine whether patients transported home by ambulance experience higher rates of return emergency department (ED) visits and readmission compared with similar patients transported home by other means. Methods: This was a retrospective cohort study conducted at a U.S. tertiary care academic hospital. Patients aged 65 years and over transported home via ambulance after hospital discharge between January and March 2012 were included. Rates of 72-h and 30-day ED revisits and 30-day hospital readmissions were calculated. Odds ratios were calculated and revisit rates between groups were compared. Results: There were 207 patients aged 65 and over transported home by ambulance. Matched controls were found for 162 patients. Compared with the matched controls, the exposed group experienced a statistically significant higher rate of 30-day ED returns (18.519% vs. 10.494%; odds ratio [OR] 1.939; p = 0.043). The exposed group also experienced a higher rate of 72-h ED returns (2.469% vs. 0.617%; OR 4.076) and 30-day readmissions (12.346% vs. 6.173%; OR 2.141), though results did not reach statistical significance. Conclusion: The study findings suggest that transport home via ambulance after hospital discharge could be predictive of a high risk of recidivism independent of established readmission risk factors. Programs that expand the role of EMS to include post-transport interventions may warrant further exploration.