Bradley captained and scored once for Toronto FC in the 2016 Eastern Conference Finals in a derby against Montreal Impact in which Toronto won on an aggregated score of 7–5, to take Toronto FC to the MLS Cup Final for the first time in their history. On December 10, 2016, Toronto lost the final at home to the Seattle Sounders 5–4 in penalty shoot-out following a goalless draw after extra-time in which Seattle had no shots on target; Bradley missed Toronto's second penalty.