On July 16, 2014, Holland agreed to a two-year contract extension with Toronto worth an annual average value of $775,000.[9]
After the 2015–16 season, he re-signed with Toronto on a one-year, $1.3 million contract.[10] 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.[11] 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.[12][11]
On July 1, 2017, as a free agent, Holland signed a two-year contract with the Montreal Canadiens, playing the second year on a one-way basis.[13] Ahead of the 2017–18 season, Holland was unable to make the Canadiens' roster out of training camp and was assigned to Montreal's AHL affiliate, the Laval Rocket. With 18 points in 20 games with Laval, on November 30, 2017, Holland was traded to the New York Rangers in exchange for Adam Cracknell.[14]
To start the 2018–19 season, Holland played with New York's AHL affiliate, the Hartford Wolf Pack. On February 18, 2019, Holland was traded to the Chicago Blackhawks in exchange for Darren Raddysh.[15] Assigned to the Rockford IceHogs, Holland continued his scoring pace in notching 7 goals and 16 points in 21 games to conclude the season.
Holland signed a one-year contract with Swedish club Djurgårdens IF of the top-tier Swedish Hockey League (SHL) in September 2021.[17] Holland played 15 games total with Djurgårdens and recorded six assists.
In an October 2021 game versus Luleå HF, Holland got into a fight and ripped an opponent's helmet off, took his own gloves off, and repeatedly punched the Luleå player in the face with his bare fists. Holland was suspended for four games and given a fine of 40,000SEK ($4,000 USD) by the Swedish Ice Hockey Association's disciplinary board. Holland's excuse was that he had never before played in a league where fighting resulted in anything other than a 5-minute penalty. He also claimed he never intended to harm an opponent.[18] The Luleå player, Fredrik Styrman, received a concussion; 10 months after the attack he had to end his hockey career due to of lingering symptoms.[19]
On March 16, 2022, Holland announced through Twitter that he had retired from professional hockey.[20] However, in an attempt to return to play, Holland signed a professional tryout (PTO) with the Colorado Avalanche in August 2023.[21] After attending both training camp and preseason, Holland accepted a reassignment to the Avalanche's AHL affiliate the Colorado Eagles, and was later signed to a one-year AHL contract to begin the 2023–24 season on October 11, 2023.[22]
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