On July 28, 2014, Winnik signed as a free agent to a one-year contract with his hometown team, the Toronto Maple Leafs, worth $1.3 million. In the 2014–15 season, Winnik proved a versatile asset for the Maple Leafs with his penalty killing abilities and scoring touch, notching 25 points in 58 appearances, and having spent time on all four lines. On February 25, 2015, with the Maple Leafs out of playoff contention, he was traded to the Pittsburgh Penguins in exchange for Zach Sill, a 2015 fourth round pick and a 2016 second round pick. In 21 games with the Penguins, Winnik collected 2 goals and 9 points but was unable to help the Penguins to a deep playoff run.