Philippines is considered as a major provider of caregiving services in Canada. Caregiving has historically been identified as feminine labour. As such, providing paid caregiving has always been associated with immigrant women. Policies are thus built to control this work and mostly they tie with the masculine culture of the society. In Canada, live-in caregiving is very gendered and masculine, and as such it discriminated men of colour. This paper is focused on a case study that was done in 2014 in Toronto. There were three paid Filipino male live-in caregivers who participated in this study. The study applied qualitative narrative research methodology. The purpose of this article is to discuss and analyse the participants’ experiences and understand how Canadian hegemonic and imperial masculinity shapes citizenship and policy in a racialised and gendered manner. Within this argument, we explore in the introduction of this article the discourse of masculinity. We also look at the history of Live-in Caregiver Program in Canada. Additionally, we deliberate and examine the participants’ narratives on gendered citizenship, gendered policy, and the nature of their job. The conclusion is based on the narratives of the Filipino male live-in caregivers and their discrimination in caregiving work on the basis of their citizenship and masculinity. The conclusion also looks at how they are able to negotiate their salary, their time to work, and how they work with their clients.