A group of University of Guelph students in HIST 2170 - Contextualizing COVID-19 have come together to chronicle the experiences of a very vulnerable and often overlooked segment of our society; the homeless, and how a global pandemic affected their health and wellbeing. Through a series of archival pages, we examine critical dates and policies in government decision making, and dive into the perspective of those without shelter during this crisis. Our focus on two cities in Ontario, Canada - Toronto and Guelph offers comparison and contrasting between municipal government responses and their effects. We seek to shine a light on how homeless people have paid the highest price for our lack of preparedness in the face of a public health emergency.