The Raptors experienced little postseason success their first 20 seasons, only getting out of the first round once, a 3-2 series win over the New York Knicks in 2001. However, that all changed in 2016. Three straight seasons with at least one playoff series win led to Canada’s first championship in 2019. That year, Toronto knocked off the Orlando Magic, Philadelphia 76ers, Milwaukee Bucks, and Golden State Warriors en route to the Larry O’Brien Trophy.