On July 1, 2015, Winnik, by this time a fan favourite in Toronto, returned to the Maple Leafs, signing as a free agent on a two-year deal. Winnik's offensive production declined from his previous season with the Maple Leafs, though he remained a concrete part of the penalty kill. On February 28, 2016, the eve of the trade deadline, Winnik was traded to the Washington Capitals, along with a 5th round selection (Beck Malenstyn) in the 2016 draft, in exchange for forward Brooks Laich, prospect defenceman Connor Carrick and a 2nd round draft pick in 2016 (Carl Grundström).