Canada relies heavily on international trade for its economic growth and success. The total trade in 2024 was worth 1.52 trillion dollars, 64% of which was with the U.S. Around 58% of total trade between the two countries took place by trucks through key Ontario land borders. The COVID-19 pandemic led to unexpected supply-chain interruptions and that included the health care sector. Part of these interruptions included the inability to move pharmaceuticals to Ontario across the border. Shortage of certain medicine supplies can have detrimental impacts on the Canadian health Care sector. To date, studies on the cross-border movements of pharmaceuticals between the U.S. and Canada are lacking. The work in this paper will fill the existing gap by characterizing these movements to understand where in the U.S. pharmaceuticals originate, and which routes and land borders are normally used to bring them into Ontario. The analysis will be based on a variety of data sources to provide a clear picture of the key U.S. markets that Ontario trades with. Scenario analysis will examine the impacts of land border closures which will cause diversion in the truck flows through alternative land border crossings to ensure uninterrupted supply-chain of pharmaceuticals to Ontario.