This study explored the linkage between immigration status and troubled sleep among recent immigrants, established immigrants and native-born in Canada. In particular, it examined whether the role of immigration status on troubled sleep differs between females and males. Using the 2012 Canadian Community Health Survey-Mental Health, logistic regression models were fitted to examine the relationship between troubled sleep and immigration status among a weighted sample of 12,932,829 women and 12,424,195 men. Findings indicate that female recent (OR 0.42, p < 0.01) and established immigrants (OR 0.74, p < 0.05) report fewer troubled sleep than their native-born counterparts. However, only male established immigrants report fewer troubled sleep (OR 0.42, p < 0.05), as male recent immigrants did not significantly differ from their native-born counterparts (OR 0.70, p > 0.05). Moreover, male recent immigrants were more likely to report troubled sleep than their female counterparts (OR 1.30, p < 0.05). Based on these findings, we discussed the potential gendered mechanisms in which immigrants' sleep is informed by social, cultural, and economic factors. We also provided several useful implications for policymakers.