After the 2015–16 season, he re-signed with Toronto on a one-year, $1.3 million contract. As the season began Holland was overshadowed by a plethora of young forward rookies including Auston Matthews, Mitch Marner and Connor Brown, among others. Due to limited roster space, Holland seldom played for the Maple Leafs, being scratched in 17 of the team's first 25 games, and seeing limited ice time in the eight games he did play. After being informed by general manager Lou Lamoriello that the team would do their best to trade him, Holland was traded to the Arizona Coyotes in exchange for a conditional draft pick in 2018 on December 9, 2016; the condition was not satisfied.