Immigrant taxi drivers in metropolitan cities are exposed to experiences of discrimination and occupation-based health risks. Given the structural differences in health care systems in the United States and Canada, we investigated the differences in reports of discrimination, health conditions and concern about health conditions between taxi drivers in New York City and Toronto, Ontario. Participants were recruited for a taxi driver Needs Assessment Survey as part of a Taxi Network needs assessment project using a street side convenience sampling technique in New York City and Toronto. The matched sample contained 33 drivers from Toronto and 33 drivers from NYC. All Toronto drivers in our sample reported having health insurance while over a quarter of NYC drivers did not have health insurance. Toronto drivers reported greater everyday and workplace discrimination. Drivers in both cities experienced higher rates than average, and reported concern about, major health conditions. We also found preliminary evidence suggesting a relationship between experiencing discrimination and reporting chronic pain. Our findings suggest the need for future research to more closely examine the associations between discrimination and health among the taxi driver population.