On June 29, 2016, Toronto FC won its fifth Canadian Championship against Vancouver 2–2 on aggregate, winning on away goals. Giovinco scored a hat-trick against D.C. United, on July 23, 2016, in a 4–1 home win, surpassing De Rosario's previous all-time record as Toronto FC's top scorer by two goals to 35 goals. In October 2016, Toronto FC clinched a playoff spot for the second straight season. The team proceeded to defeat the Philadelphia Union at BMO Field in the Eastern Conference Knockout Round to record their first-ever playoff win and to secure entry into the first Eastern Conference Semi-final in franchise history. Toronto FC defeated New York City FC 7–0 on aggregate to reach an all-Canadian Eastern Conference Finals derby against Montreal Impact. Montreal won the first leg of the Conference Championship, 3–2 at the Olympic Stadium in Montreal on November 22. Toronto beat Montreal 5–2 in extra time in the return leg at BMO Field in Toronto on November 30, winning on an aggregated score of 7–5, making Toronto FC the first Canadian team to compete in an MLS Cup Final. On December 10, Toronto lost the final at home to the Seattle Sounders 5–4 in penalty shoot-out following a goalless draw after extra-time.